Subscribe to RSS
DOI: 10.1055/s-0035-1560378
Cobalt-Catalysed Bond Formation Reactions; Part 2
Publication History
Received: 07 October 2015
Accepted after revision: 05 November 2015
Publication Date:
03 December 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201604/lookinside/thumbnails/ss-2015-e0586-r_10-1055_s-0035-1560378-1.jpg)
Dedicated to Paul Knochel on the occasion of his 60th birthday.
Abstract
This review summarises the cobalt-catalysed reactions of the years 2008 through 2014. Covered are addition reactions, such as the hydrogenation of double bonds, the addition of C–H bonds to double and triple bonds, C–H activation reactions, cobalt-catalysed cross-coupling reactions and selected additions of H–B and H–Si bonds to unsaturated starting materials. The cobalt-catalysed cycloadditions range from cyclopropanations, [2+2], Pauson–Khand reactions, [2+2+2], [4+2], [6+2] cycloadditions as well as benzannulations. Also covered are Nicholas reactions, cobalt-catalysed Jacobsen’s kinetic resolution of epoxides as well as selected miscellaneous cobalt-catalysed processes mainly for carbon–carbon bond formations.
1 Introduction
2 Addition Reactions
3 Homo- and Cross-Coupling Reactions
4 Jacobsen Kinetic Resolution of Epoxides
5 Nicholas Reactions
6 Cycloaddition Reactions
7 Miscellaneous
8 Conclusion
-
References
- 1 For the preceding review, see: Hess W, Treutwein J, Hilt G. Synthesis 2008; 3537-3562
- 2 For a recent review on cobalt-catalysed reactions with π-systems, see: Gandeepan P, Cheng C.-H. Acc. Chem. Res. 2015; 48: 1194-1206
-
3 For a recent review on cobalt-catalysed C–H activations, see: Gao K, Yoshikai N. Acc. Chem. Res. 2014; 47: 1208-1219
- 4 For a recent review on asymmetric cobalt-catalysed transformations, see: Pellissier H, Clavier H. Chem. Rev. 2014; 114: 2775-2823
- 5 For a recent review on cobalt-catalysed cycloadditions, see: Domínguez G, Pérez-Castells J. In Comprehensive Organic Synthesis II . Vol. 5. Knochel P, Molander GA. Elsevier; Amsterdam: 2014: 1537-1581
- 6 Tsubo T, Chen H.-H, Yokomori M, Fukui K, Kikuchi S, Yamada T. Chem. Lett. 2012; 41: 780-782
- 7 Tsubo T, Yokomori M, Chen H.-H, Komori-Orisaku K, Kikuchi S, Koide Y, Yamada T. Chem. Lett. 2012; 41: 783-785
- 8 Tsubo T, Chen H.-H, Yokomori M, Kikuchi S, Yamada T. Bull. Chem. Soc. Jpn. 2013; 86: 983-986
- 9 Hayashi T, Kikuchi S, Asano Y, Endo Y, Yamada T. Org. Process Res. Dev. 2012; 16: 1235-1240
- 10 Ashizawa T, Tanaka S, Yamada T. Org. Lett. 2008; 10: 2521-2524
- 11 Dombray T, Helleu C, Darcel C, Sortais J.-B. Adv. Synth. Catal. 2013; 355: 3358-3362
- 12 Niu Q, Sun H, Li X, Klein H.-F, Flörke U. Organometallics 2013; 32: 5235-5238
- 13 Sauer DC, Wadepohl H, Gade LH. Inorg. Chem. 2012; 51: 12948-12958
- 14 Inagaki T, Phong LT, Furuta A, Ito J.-I, Nishiyama H. Chem. Eur. J. 2010; 16: 3090-3096
- 15 Yu F, Zhang X.-C, Wu F.-F, Zhou J.-N, Fang W, Wu J, Chan AS. C. Org. Biomol. Chem. 2011; 9: 5652-5654
- 16 Gärtner D, Welther A, Rad BR, Wolf R, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2014; 53: 3722-3726
- 17 Friedfeld MR, Margulieux GW, Schaefer BA, Chirik PJ. J. Am. Chem. Soc. 2014; 136: 13178-13181
- 18 Friedfeld MR, Shevlin M, Hoyt JM, Krska SW, Tudge MT, Chirik PJ. Science 2013; 342: 1076-1080
- 19 Monfette S, Turner ZR, Semproni SP, Chirik PJ. J. Am. Chem. Soc. 2012; 134: 4561-4564
- 20 For a mechanistic study, see: Hopmann KH. Organometallics 2013; 32: 6388-6399
- 21 Aldea L, Fraile JM, García-Marín H, García JI, Herrerías CI, Mayoral JA, Pérez I. Green Chem. 2010; 12: 435-440
- 22 Iwasaki K, Wan KK, Oppedisano A, Crossley SW. M, Shenvi RA. J. Am. Chem. Soc. 2014; 136: 1300-1303
- 23 Kumar V, Sharma U, Verma PK, Kumar N, Singh B. Adv. Synth. Catal. 2012; 354: 870-878
- 24 Mo Z, Xiao J, Gao Y, Deng L. J. Am. Chem. Soc. 2014; 136: 17414-17417
- 25 Huang K.-H, Isobe M. Eur. J. Org. Chem. 2014; 4733-4740
- 26 Konno T, Taku K.-I, Yamada S, Moriyasu K, Ishihara T. Org. Biomol. Chem. 2009; 7: 1167-1170
- 27 Chen W.-W, Bi H.-P, Li C.-J. Synlett 2010; 475-479
- 28 Sawano T, Ou K, Nishimura T, Hayashi T. Chem. Commun. 2012; 48: 6106-6108
- 29 Nishimura T, Sawano T, Ou K, Hayashi T. Chem. Commun. 2011; 47: 10142-10144
- 30 For cobalt-catalysed conjugate 1,4-addition of aryl boronic esters, see: Chen M.-H, Mannathan S, Lin P.-S, Cheng C.-H. Chem. Eur. J. 2012; 18: 14918-14922
- 31 For cobalt-catalysed conjugate 1,4-addition of aryl zinc reagents, see: Amatore M, Gosmini C. Synlett 2009; 1073-1076
- 32 Sawano T, Ashouri A, Nishimura T, Hayashi T. J. Am. Chem. Soc. 2012; 134: 18936-18939
- 33 Sakurada T, Sugiyama Y.-K, Okamoto S. J. Org. Chem. 2013; 78: 3583-3591
- 34 Chen J, Xi T, Ren X, Cheng B, Guo J, Lu Z. Org. Chem. Front. 2014; 1: 1306-1309
- 35 Obligacion JV, Chirik PJ. J. Am. Chem. Soc. 2013; 135: 19107-19110
- 36 Atienza CC. H, Diao T, Weller KJ, Nye SA, Lewis KM, Delis JG. P, Boyer JL, Roy AK, Chirik PJ. J. Am. Chem. Soc. 2014; 136: 12108-12118
- 37 Mannathan S, Cheng C.-H. Chem. Commun. 2010; 46: 1923-1925
- 38 Mannathan S, Cheng C.-H. Chem. Eur. J. 2012; 18: 11771-11777
- 39 Wei C.-H, Mannathan S, Cheng C.-H. J. Am. Chem. Soc. 2011; 133: 6942-6944
- 40 Wei C.-H, Mannathan S, Cheng C.-H. Angew. Chem. Int. Ed. 2012; 51: 10592-10595
- 41 Hilt G, Erver F, Harms K. Org. Lett. 2011; 13: 304-307
- 42 Hilt G, Paul A, Treutwein J. Org. Lett. 2010; 12: 1536-1539
- 43 Sušnik P, Hilt G. Organometallics 2014; 33: 5907-5910
- 44 Erver F, Hilt G. J. Org. Chem. 2012; 77: 5215-5219
- 45 Hilt G. Synlett 2011; 1654-1659
- 46 RajanBabu TV. Synlett 2009; 853-885
- 47 Hilt G. Eur. J. Org. Chem. 2012; 4441-4451
- 48 Saini V, Strokes BJ, Sigman MS. Angew. Chem. Int. Ed. 2013; 52: 11206-11220
- 49 Grutters MM. P, van der Vlugt JI, Pei Y, Mills AM, Lutz M, Spek AL, Müller C, Moberg C, Vogt D. Adv. Synth. Catal. 2009; 351: 2199-2208
- 50 Toti A, Giambastiani G, Bianchini C, Meli A, Luconi L. Adv. Synth. Catal. 2008; 350: 1855-1866
- 51 RajanBabu TV. Chem. Rev. 2003; 103: 2845-2860
- 52 Page JP, RajanBabu TV. J. Am. Chem. Soc. 2012; 134: 6556-6559
- 53 Sharma RK, RajanBabu TV. J. Am. Chem. Soc. 2010; 132: 3295-3297
- 54 Vogt D. Angew. Chem. Int. Ed. 2010; 49: 7166-7168
- 55 Arndt M, Dindaroğlu M, Schmalz H.-G, Hilt G. Synthesis 2012; 44: 3534-3542
- 56 Hilt G, Treutwein J. Chem. Commun. 2009; 1395-1397
- 57 Arndt M, Reinhold A, Hilt G. J. Org. Chem. 2010; 75: 5203-5210
- 58 Erver F, Hilt G. Org. Lett. 2011; 13: 5700-5703
- 59 Erver F, Kuttner JR, Hilt G. J. Org. Chem. 2012; 77: 8375-8385. Iron powder was originally added in the meta-selective Diels–Alder reaction catalysed by cobalt-imine-type complexes to suppress side-reactions
- 60 Erver F, Hilt G. Org. Lett. 2012; 14: 1884-1887
- 61 Hilt G, Danz M, Treutwein J. Org. Lett. 2009; 11: 3322-3325
- 62 Hilt G, Roesner S. Synthesis 2011; 662-668
- 63 Arndt M, Dindaroğlu M, Schmalz H.-G, Hilt G. Org. Lett. 2011; 13: 6236-6239
- 64 Bohn MA, Schmidt A, Hilt G, Dindaroğlu M, Schmalz H.-G. Angew. Chem. Int. Ed. 2011; 50: 9689-9693
- 65 Schmidt A, Hilt G. Org. Lett. 2013; 15: 2708-2711
- 66 Schmidt A, Maiterth E, Hilt G. Synthesis 2014; 46: 2040-2044
- 67 Kersten L, Hilt G. Adv. Synth. Catal. 2012; 354: 863-869
- 68 Kersten L, Roesner S, Hilt G. Org. Lett. 2010; 12: 4920-4923
- 69 Hilt G, Arndt M, Weske DF. Synthesis 2010; 1321-1324
- 70 Chen Q.-A, Kim DK, Dong VM. J. Am. Chem. Soc. 2014; 136: 3772-3775
- 71 Zhang F, Du P, Chen J, Wang H, Luo Q, Wan X. Org. Lett. 2014; 16: 1932-1935
- 72 Timsina YN, Biswas S, RajanBabu TV. J. Am. Chem. Soc. 2014; 136: 6215-6218
- 73 Pünner F, Schmidt A, Hilt G. Angew. Chem. Int. Ed. 2012; 51: 1270-1273
- 74 Chen C, Dugan TR, Brennessel WW, Weix DJ, Holland PL. J. Am. Chem. Soc. 2014; 136: 945-955
- 75 Weding N, Spannenberg A, Jackstell R, Hapke M. Organometallics 2012; 31: 5660-5663
- 76 Ackermann L. J. Org. Chem. 2014; 79: 8948-8954
- 77 Punji B, Song W, Shevchenko GA, Ackermann L. Chem. Eur. J. 2013; 19: 10605-10610
- 78 Chen Q, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 428-429
- 79 Ilies L, Chen Q, Zeng X, Nakamura E. J. Am. Chem. Soc. 2011; 133: 5221-5223
- 80 Qian YY, Wong KL, Zhang MW, Kwok TY, To CT, Chan KS. Tetrahedron Lett. 2012; 53: 1571-1575
- 81 Gao K, Yamakawa T, Yoshikai N. Synthesis 2014; 46: 2024-2039
-
82 Song W, Ackermann L. Angew. Chem. Int. Ed. 2012; 51: 8251-8254
- 83 Gao K, Lee P.-S, Fujita T, Yoshikai N. J. Am. Chem. Soc. 2010; 132: 12249-12251
- 84 Ding Z, Yoshikai N. Beilstein J. Org. Chem. 2012; 8: 1536-1542
- 85 Gao K, Yoshikai N. Chem. Commun. 2012; 48: 4305-4307
- 86 Yoshino T, Ikemoto H, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2013; 52: 2207-2211
- 87 Gao K, Paira R, Yoshikai N. Adv. Synth. Catal. 2014; 356: 1486-1490
- 88 Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4684-4687
- 89 Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4688-4690
- 90 Ding Z, Yoshikai N. Angew. Chem. Int. Ed. 2012; 51: 4698-4701
- 91 Gao K, Yoshikai N. J. Am. Chem. Soc. 2011; 133: 400-402
- 92 Yoshikai N. Synlett 2011; 1047-1051
- 93 Yang Z, Yu H, Fu Y. Chem. Eur. J. 2013; 19: 12093-12103
- 94 Lee P.-S, Fujita T, Yoshikai N. J. Am. Chem. Soc. 2011; 133: 17283-17295
- 95 Yamakawa T, Yoshikai N. Tetrahedron 2013; 69: 4459-4465
- 96 Lee P.-S, Yoshikai N. Angew. Chem. Int. Ed. 2013; 52: 1240-1244
- 97 Dong J, Lee P.-S, Yoshikai N. Chem. Lett. 2013; 42: 1140-1142
- 98 Ding Z, Yoshikai N. Angew. Chem. Int. Ed. 2013; 52: 8574-8578
- 99 Gao K, Yoshikai N. Angew. Chem. Int. Ed. 2011; 50: 6888-6892
-
100 Gao K, Yoshikai N. J. Am. Chem. Soc. 2013; 135: 9279-9282
-
101 Gao K, Lee P.-S, Long C, Yoshikai N. Org. Lett. 2012; 14: 4234-4237
- 102 Chen Q, Ilies L, Yoshikai N, Nakamura E. Org. Lett. 2011; 13: 3232-3234
- 103 Li B, Wu Z.-H, Gu Y.-F, Sun C.-L, Wang B.-Q, Shi Z.-J. Angew. Chem. Int. Ed. 2011; 50: 1109-1113
- 104 Murakami K, Yorimitsu H, Oshima K. Org. Lett. 2009; 11: 2373-2375
- 105 Tan B.-H, Dong J, Yoshikai N. Angew. Chem. Int. Ed. 2012; 51: 9610-9614
- 106 Ding Z, Yoshikai N. Org. Lett. 2010; 12: 4180-4183
- 107 Ding Z, Yoshikai N. Synthesis 2011; 2561-2566
- 108 Andou T, Saga Y, Komai H, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2013; 52: 3213-3216
- 109 Yamamoto S, Saga Y, Andou T, Matsunaga S, Kanai M. Adv. Synth. Catal. 2014; 356: 401-405
- 110 Gosmini C, Bégouin J.-M, Moncomble A. Chem. Commun. 2008; 3221-3233
- 111 Amatore M, Gosmini C. Angew. Chem. Int. Ed. 2008; 47: 2089-2092
- 112 Moncomble A, Le Floch P, Gosmini C. Chem. Eur. J. 2009; 15: 4770-4774
- 113 Truong T, Alvarado J, Tran LD, Daugulis O. Org. Lett. 2010; 12: 1200-1203
- 114 Chen S.-Y, Zhang J, Li Y.-H, Wen J, Bian S.-Q, Yu X.-Q. Tetrahedron Lett. 2009; 50: 6795-6797
- 115 Bégouin J.-M, Claudel S, Gosmini C. Synlett 2009; 3192-3194
- 116 Bégouin J.-M, Gosmini C. J. Org. Chem. 2009; 74: 3221-3224
- 117 Jin M.-Y, Yoshikai N. J. Org. Chem. 2011; 76: 1972-1978
- 118 Araki K, Inoue M. Tetrahedron 2013; 69: 3913-3918
- 119 Hamaguchi H, Uemura M, Yasui H, Yorimitsu H, Oshima K. Chem. Lett. 2008; 37: 1178-1179
- 120 Hatakeyama T, Hashimoto S, Ishizuka K, Nakamura M. J. Am. Chem. Soc. 2009; 131: 11949-11963
- 121 Gülak S, Stepanek O, Malberg J, Rad BR, Kotora M, Wolf R, Jacobi von Wangelin A. Chem. Sci. 2013; 4: 776-784
- 122 Mayer M, Czaplik WM, Jacobi von Wangelin A. Synlett 2009; 2919-2923
- 123 Moncomble A, Le Floch P, Lledos A, Gosmini C. J. Org. Chem. 2012; 77: 5056-5062
- 124 Mao J, Liu F, Wang M, Wu L, Zheng B, Liu S, Zhong J, Bian Q, Walsh PJ. J. Am. Chem. Soc. 2014; 136: 17662-17668
- 125 Cahiez G, Chaboche C, Duplais C, Moyeux A. Org. Lett. 2009; 11: 277-280
- 126 Cahiez G, Chaboche C, Duplais C, Guilliani A, Moyeux A. Adv. Synth. Catal. 2008; 350: 1484-1488
- 127 Iwasaki T, Takagawa H, Okamoto K, Singh SP, Kuniyasu H, Kambe N. Synthesis 2014; 46: 1583-1592
- 128 Przyojski JA, Arman HD, Tonzetich ZJ. Organometallics 2013; 32: 723-732
- 129 Czaplik WM, Mayer M, Jacobi von Wangelin A. Synlett 2009; 2931-2934
- 130 Hsu S.-F, Ko C.-W, Wu Y.-T. Adv. Synth. Catal. 2011; 353: 1756-1762
- 131 Nicolas L, Izquierdo E, Angibaud P, Stansfield I, Meerpoel L, Reymond S, Cossy J. J. Org. Chem. 2013; 78: 11807-11814
- 132 Barré B, Gonnard L, Campagne R, Reymond S, Marin J, Ciapetti P, Brellier M, Guérinot A, Cossy J. Org. Lett. 2014; 16: 6160-6163
- 133 Hammann JM, Streib AK, Knochel P. Org. Lett. 2014; 16: 6500-6503
- 134 Despiau CF, Dominey AP, Harrowven DC, Linclau B. Eur. J. Org. Chem. 2014; 4335-4341
- 135 Nicolas L, Angibaud P, Stansfield I, Bonnet P, Meerpoel L, Reymond S, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 11101-11104
- 136 Schaus SE, Brandes BD, Larrow JF, Tokunaga M, Hansen KB, Gould AE, Furrow ME, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 1307-1315
- 137 Lee K.-Y, Lee C.-Y, Kim G.-J. React. Kinet. Catal. Lett. 2008; 93: 75-83
- 138 Key RE, Venkatasubbaiah K, Jones CW. J. Mol. Catal. A: Chem. 2013; 366: 1-7
- 139 Kawthekar RB, Bi W.-T, Kim G.-J. Appl. Organomet. Chem. 2008; 22: 583-591
- 140 Kawthekar RB, Kim G.-J. Helv. Chim. Acta 2008; 91: 317-332
- 141 Nielsen LP. C, Stevenson CP, Blackmond DG, Jacobsen EN. J. Am. Chem. Soc. 2004; 126: 1360-1362
- 142 Liu Y, Rawlston J, Swann AT, Takatani T, Sherrill CD, Ludovice PJ, Weck M. Chem. Sci. 2011; 2: 429-438
- 143 Haak RM, Belmonte MM, Escudero-Adán EC, Benet-Buchholz J, Kleij AW. Dalton Trans. 2010; 39: 593-602
- 144 Zhu X, Venkatasubbaiah K, Weck M, Jones CW. J. Mol. Catal. A: Chem. 2010; 329: 1-6
- 145 Venkatasubbaiah K, Gill CS, Takatani T, Sherrill CD, Jones CW. Chem. Eur. J. 2009; 15: 3951-3955
- 146 Wezenberg SJ, Kleij AW. Adv. Synth. Catal. 2010; 352: 85-91
- 147 Zheng X, Jones CW, Weck M. Adv. Synth. Catal. 2008; 350: 255-261
- 148 Kim Y.-S, Guo X.-F, Kim G.-J. Top. Catal. 2009; 52: 197-204
- 149 Gill CS, Venkatasubbaiah K, Pham NT. S, Weck M, Jones CW. Chem. Eur. J. 2008; 14: 7306-7313
- 150 Beigi M, Roller S, Haag R, Liese A. Eur. J. Org. Chem. 2008; 2135-2141
- 151 Kureshy RI, Prathap KJ, Agrawal S, Kumar M, Khan N.-UH, Abdi SH. R, Bajaj HC. Eur. J. Org. Chem. 2009; 2863-2871
- 152 Guo X.-F, Kim Y.-S, Kim G.-J. Top. Catal. 2009; 52: 153-160
- 153 Lee K.-Y, Lee C.-Y, Kim G.-J. Bull. Korean Chem. Soc. 2009; 30: 389-396
- 154 Kim Y.-S, Lee C.-Y, Kim G.-J. Bull. Korean Chem. Soc. 2009; 30: 1771-1777
- 155 Kim Y.-S, Guo X.-F, Kim G.-J. Chem. Commun. 2009; 4296-4298
- 156 Kim Y.-S, Guo X.-F, Kim G.-J. Catal. Today 2010; 150: 91-99
- 157 Belser T, Jacobsen EN. Adv. Synth. Catal. 2008; 350: 967-971
- 158 Chowdhury PS, Gupta P, Kumar P. Tetrahedron Lett. 2009; 50: 7018-7020
- 159 Brimble MA, Finch OC, Heapy AM, Fraser JD, Furkert DP, O’Connor PD. Tetrahedron 2011; 67: 995-1001
- 160 Tripathi D, Pandey SK, Kumar P. Tetrahedron 2009; 65: 2226-2231
- 161 Sabitha G, Chandrashekhar G, Yadagiri K, Yadav JS. Tetrahedron Lett. 2010; 51: 3824-3826
- 162 Babu KV, Sharma GV. M. Tetrahedron: Asymmetry 2008; 19: 577-583
- 163 Kiran IN. C, Reddy RS, Suryavanshi G, Sudalai A. Tetrahedron Lett. 2011; 52: 438-440
- 164 Raj IV. P, Sudalai A. Tetrahedron Lett. 2008; 49: 2646-2648
- 165 Reddy RS, Chouthaiwale PV, Suryavanshi G, Chavan VB, Sudalai A. Chem. Commun. 2010; 46: 5012-5014
- 166 Saikia PP, Goswami A, Baishya G, Barua NC. Tetrahedron Lett. 2009; 50: 1328-1330
- 167 Muthukrishnan M, Mujahid M, Sasikumar M, Mujumdar P. Tetrahedron: Asymmetry 2011; 22: 1353-1357
- 168 Sasikumar M, Nikalje MD, Muthukrishnan M. Tetrahedron: Asymmetry 2009; 20: 2814-2817
- 169 Narsaiah AV, Nagaiah B. Synthesis 2010; 2705-2707
- 170 Gadakh SK, Reddy RS, Sudalai A. Tetrahedron: Asymmetry 2012; 23: 898-903
- 171 Loy RN, Jacobsen EN. J. Am. Chem. Soc. 2009; 131: 2786-2787
- 172 Kalow JA, Doyle AG. J. Am. Chem. Soc. 2010; 132: 3268-3269
- 173 Kalow JA, Doyle AG. J. Am. Chem. Soc. 2011; 133: 16001-16012
- 174 Viera I, Manta E, González L, Mahler G. Tetrahedron: Asymmetry 2010; 21: 631-635
- 175 Dzygiel P, Reeve TB, Piarulli U, Krupicka M, Tvaroska I, Gennari C. Eur. J. Org. Chem. 2008; 1253-1264
- 176 Hyun MY, Kim SH, Song YS, Lee HG, Jo YD, Kim JH, Hwang IH, Noh JY, Kang J, Kim C. J. Org. Chem. 2012; 77: 7307-7312
- 177 Yamada T, Higano S, Yano T, Yamashita Y. Chem. Lett. 2009; 38: 40-41
- 178 For a perspective article, see: Bromfield KM, Gradén H, Ljungdahl N, Kann N. Dalton Trans. 2009; 26: 5051-5061
- 179 Díaz Díaz D, Martín VS. Molbank 2009; 2009: M612
- 180 Carrillo R, Martín T, López-Rodríguez M, Pinacho Crisóstomo F. Org. Lett. 2014; 16: 552-555
- 181 Kihara N, Kidoba K. Org. Lett. 2009; 11: 1313-1316
- 182 Tsukada Y, Yamada K, Kunishima M. Tetrahedron Lett. 2011; 52: 3358-3360
- 183 Hagendorn T, Bräse S. RSC Adv. 2014; 4: 15493-15495
- 184 Mukai C, Kojima T, Kawamura T, Inagaki F. Tetrahedron 2013; 69: 7659-7669
- 185 Green JR. Eur. J. Org. Chem. 2008; 6053-6062
- 186 Amiralaei S, Gauld J, Green JR. Chem. Eur. J. 2011; 17: 4157-4165
- 187 Amiralaei S, Green JR. Chem. Commun. 2008; 4971-4973
- 188 Hernández JN, Ramírez MA, Rodríguez ML, Martín VS. Org. Lett. 2008; 10: 2349-2352
- 189 Tyrrell E, Mazloumi K, Banti D, Sajdak P, Sinclair A, Le Greysley A. Tetrahedron Lett. 2012; 53: 4280-4282
- 190 Brawn P, Tyrrell E, Carew M, Tesfa KH, Greenwood I. Tetrahedron 2012; 68: 10040-10048
- 191 Ljungdahl N, Parera Pera N, Andersson KH. O, Kann N. Synlett 2008; 394-398
- 192 Tumanov VV, Zatonsky GV, Smit WA. Tetrahedron 2010; 66: 2156-2161
- 193 Mitachi K, Shimizu T, Miyashita M, Tanino K. Tetrahedron Lett. 2010; 51: 3983-3986
- 194 Lobo F, Gómez AM, Miranda S, López JC. Chem. Eur. J. 2014; 20: 10492-10502
- 195 Gómez AM, Lobo F, Pérez de las Vacas D, Valverde S, López JC. Chem. Commun. 2010; 46: 6159-6161
- 196 Valderas C, de la Torre MC, Fernández I, Paz Muñoz M, Sierra MA. Organometallics 2013; 32: 951-956
- 197 Kawano M, Kiuchi T, Matsuo J.-I, Ishibashi H. Tetrahedron Lett. 2012; 53: 432-434
- 198 Shao H, Zhang X.-M, Wang S.-H, Zhang F.-M, Tu Y.-Q, Yang C. Chem. Commun. 2014; 50: 5691-5694
- 199 Krafft ME, Campbell MJ, Kerrigan S, Cran JW. Tetrahedron Lett. 2011; 52: 1090-1092
- 200 Isaji H, Nakazaki A, Isobe M, Nishikawa T. Chem. Lett. 2011; 40: 1079-1081
- 201 Djurdjevic S, Yang F, Green JR. J. Org. Chem. 2010; 75: 8241-8251
- 202 Green JR, Tjeng AA. J. Org. Chem. 2009; 74: 7411-7416
- 203 Rodríguez-López J, Pinacho Crisóstomo F, Ortega N, López-Rodríguez M, Martín VS, Martín T. Angew. Chem. Int. Ed. 2013; 52: 3659-3662
- 204 Taj RA, Green JR. J. Org. Chem. 2010; 75: 8258-8270
- 205 Taj RA, Abhayawardhana A, Green JR. Synlett 2009; 292-296
- 206 Rodríguez-López J, Ortega N, Martín VS, Martín T. Chem. Commun. 2014; 50: 3685-3688
- 207 Ortega N, Martín T, Martín VS. Eur. J. Org. Chem. 2009; 554-563
- 208 Ortega N, Martín VS, Martín T. J. Org. Chem. 2010; 75: 6660-6672
- 209 Kolodziej I, Green JR. Synlett 2011; 2397-2401
- 210 Tsao K.-W, Cheng C.-Y, Isobe M. Org. Lett. 2012; 14: 5274-5277
- 211 Tyrell E, Hunie Tesfa K, Greenwood I, Mann A. Bioorg. Med. Chem. 2008; 18: 1237-1240
- 212 Djurdjevic S, Green JR. Org. Lett. 2013; 15: 5468-5471
- 213 Lavy S, Pérez-Luna A, Kündig EP. Synlett 2008; 2621-2624
- 214 Melikyan GG, Spencer R. Tetrahedron 2010; 66: 5321-5328
- 215 Melikyan GG, Wild C, Toure P. Organometallics 2008; 27: 1569-1581
- 216 Melikyan GG, Rivas B, Harutyunyan S, Carlson L, Sepanian R. Organometallics 2012; 31: 1653-1663
- 217 Melikyan GG, Sepanian R, Spencer R, Rowe A, Toure P. Organometallics 2009; 28: 5541-5549
- 218 Morandi B, Mariampillai B, Carriera EM. Angew. Chem. Int. Ed. 2011; 50: 1101-1104
- 219 Langlotz BK, Wadepohl H, Gade LH. Angew. Chem. Int. Ed. 2008; 47: 4670-4674
- 220 Fantauzzi S, Gallo E, Rose E, Raoul N, Caselli A, Issa S, Ragaini F, Cenini S. Organometallics 2008; 27: 6143-6151
- 221 Zhu S, Perman JA, Zhang XP. Angew. Chem. Int. Ed. 2008; 47: 8460-8463
-
222 Zhu S, Ruppel JV, Lu H, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2008; 130: 5042-5043
-
223 Zhu S, Xu X, Perman JA, Zhang XP. J. Am. Chem. Soc. 2010; 132: 12796-12799
- 224 Xu X, Lu H, Ruppel JV, Cui X, Lopez de Mesa S, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2011; 133: 15292-15295
- 225 Ruppel JV, Gauthier TJ, Snyder NL, Perman JA, Zhang XP. Org. Lett. 2009; 11: 2273-2276
- 226 Ruppel JV, Jones JE, Huff CA, Kamble RM, Chen Y, Zhang XP. Org. Lett. 2008; 10: 1995-1998
- 227 Jones JE, Ruppel JV, Gao G.-Y, Moore TM, Zhang XP. J. Org. Chem. 2008; 73: 7260-7265
- 228 Tao J, Jin L.-M, Zhang XP. Beilstein J. Org. Chem. 2014; 10: 1282-1289
- 229 Cui X, Xu X, Lu H, Zhu S, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2011; 133: 3304-3307
- 230 White JD, Shaw S. Org. Lett. 2014; 16: 3880-3883
- 231 Harcourt EM, Yonis SR, Lynch DE, Hamilton DG. Organometallics 2008; 27: 1653-1656
- 232 Jana R, Kumar MS, Singh N, Elias AJ. J. Organomet. Chem. 2008; 693: 3780-3786
- 233 Bertrand G, Tortech L, Fichou D, Malacria M, Aubert C, Gandon V. Organometallics 2012; 31: 126-132
-
234 Vázquez-Romero A, Cárdenas L, Blasi E, Verdaguer X, Riera A. Org. Lett. 2009; 11: 3104-3107
- 235 Fustero S, Lázaro R, Aiguabella N, Riera A, Simón-Fuentes A, Barrio P. Org. Lett. 2014; 16: 1224-1227
-
236 Lledó A, Fuster A, Revés M, Verdaguer X, Riera A. Chem. Commun. 2013; 49: 3055-3057
-
237 Revés M, Lledó A, Ji Y, Blasi E, Riera A, Verdaguer X. Org. Lett. 2012; 14: 3534-3537
- 238 Vázquez-Romero A, Rodríguez J, Lledó A, Verdaguer X, Riera A. Org. Lett. 2008; 10: 4509-4512
- 239 Ji Y, Riera A, Verdaguer X. Org. Lett. 2009; 11: 4346-4349
- 240 Revés M, Achard T, Solà J, Riera A, Verdaguer X. J. Org. Chem. 2008; 73: 7080-7087
-
241 Fager-Jokela E, Muuronen M, Patzschke M, Helaja J. J. Org. Chem. 2012; 77: 9134-9147
-
242 Moulton BE, Whitwood AC, Duhme-Klair AK, Lynam JM, Fairlamb IJ. S. J. Org. Chem. 2011; 76: 5320-5334
- 243 Moulton BE, Lynam JM, Duhme-Klair AK, Zheng W, Lin Z, Fairlamb IJ. S. Org. Biomol. Chem. 2010; 8: 5398-5403
- 244 Solà J, Revés M, Riera A, Verdaguer X. Angew. Chem. Int. Ed. 2007; 46: 5020-5023
-
245 Aiguabella N, Pesquer A, Verdaguer X, Riera A. Org. Lett. 2013; 15: 2696-2699
- 246 Ji Y, Riera A, Verdaguer X. Eur. J. Org. Chem. 2011; 1438-1442
- 247 For a mechanistic study on the use of phosphine ligands in PKRs, see: Ferrer C, Benet-Buchholz J, Riera A, Verdaguer X. Chem. Eur. J. 2010; 16: 8340-8346
- 248 Fager-Jokela E, Muuronen M, Khaizourane H, Vázquez-Romero A, Verdaguer X, Riera A, Helaja J. J. Org. Chem. 2014; 79: 10999-11010
-
249 Kizirian J.-C, Aiguabella N, Pesquer A, Fustero S, Bello P, Verdaguer X, Riera A. Org. Lett. 2010; 12: 5620-5623
-
250 Aiguabella N, del Pozo C, Verdaguer X, Fustero S, Riera A. Angew. Chem. Int. Ed. 2013; 52: 5355-5359
- 251 Aiguabella N, Arce EM, del Pozo C, Verdaguer X, Riera A. Molecules 2014; 19: 1763-1774
- 252 Olier C, Azzi N, Gil G, Gastaldi S, Bertrand MP. J. Org. Chem. 2008; 73: 8469-8473
-
253 Closser KD, Quintal MM, Shea KM. J. Org. Chem. 2009; 74: 3680-3688
- 254 Higuchi Y, Atobe S, Tanaka M, Kamiya I, Yamamoto T, Nomoto A, Sonoda M, Ogawa A. Organometallics 2011; 30: 4539-4543
- 255 Kawatsura M, Kajita K, Hayase S, Itoh T. Synlett 2010; 1243-1246
- 256 Xu R, Winget P, Clark T. Eur. J. Inorg. Chem. 2008; 2874-2883
- 257 Gandon V In Transition-Metal-Mediated Aromatic Ring Construction . Tanaka K. Wiley-VCH; Weinheim: 2013: 3-35
-
258 Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M. Org. React. 2007; 68: 1-302
- 259 Iannazzo L, Kotera N, Malacria M, Aubert C, Gandon V. J. Organomet. Chem. 2011; 696: 3906-3908
- 260 Iannazzo L, Vollhardt KP. C, Malacria M, Aubert C, Gandon V. Eur. J. Org. Chem. 2011; 3283-3292
- 261 Sugiyama Y.-K, Kato R, Sakurada T, Okamoto S. J. Am. Chem. Soc. 2011; 133: 9712-9715
- 262 Watanabe J.-I, Sugiyama Y.-K, Nomura A, Azumatei S, Goswami A, Saino N, Okamoto S. Macromolecules 2010; 43: 2213-2218
- 263 Michaux J, Poirot R, Einhorn J, Bessières B. Tetrahedron Lett. 2014; 55: 2849-2852
- 264 Saino N, Kawaji T, Ito T, Matsushita Y, Okamoto S. Tetrahedron Lett. 2010; 51: 1313-1316
- 265 Heller B, Hapke M, Fischer C, Andronova A, Starý I, Stará IG. J. Organomet. Chem. 2013; 723: 98-102
- 266 Sehnal P, Krausová Z, Teplý F, Stará IG, Starý I, Rulíšek L, Šaman D, Císařová I. J. Org. Chem. 2008; 73: 2074-2082
- 267 Hilt G, Hengst C, Hess W. Eur. J. Org. Chem. 2008; 2293-2297
- 268 Xu L, Yu R, Wang Y, Chen J, Yang Z. J. Org. Chem. 2013; 78: 5744-5750
- 269 Han B, Hu P, Wang B.-Q, Redshaw C, Zhao K.-Q. Beilstein J. Org. Chem. 2013; 9: 2852-2861
- 270 Eichman CC, Bragdon JP, Stambuli JP. Synlett 2011; 1109-1112
- 271 Sugiyama Y.-K, Kariwa T, Sakurada T, Okamoto S. Synlett 2012; 23: 2549-2553
- 272 Nicolaus N, Strauss S, Neudörfl J.-M, Prokop A, Schmalz H.-G. Org. Lett. 2009; 11: 341-344
- 273 Kesenheimer C, Kalogerakis A, Meißner A, Groth U. Chem. Eur. J. 2010; 16: 8805-8821
-
274 Geny A, Agenet N, Iannazzo L, Malacria M, Aubert C, Gandon V. Angew. Chem. Int. Ed. 2009; 48: 1810-1813
- 275 Thiel I, Jiao H, Spannenberg A, Hapke M. J. Organomet. Chem. 2014; 763: 60-64
- 276 Weding N, Jackstell R, Jiao H, Spannenberg A, Hapke M. Adv. Synth. Catal. 2011; 353: 3423-3433
- 277 Thiel I, Jiao H, Spannenberg A, Hapke M. Chem. Eur. J. 2013; 19: 2548-2554
-
278 Hapke M, Weding N, Spannenberg A. Organometallics 2010; 29: 4298-4304
- 279 Thiel I, Spannenberg A, Hapke M. ChemCatChem 2013; 5: 2865-2868
- 280 Hilt G, Paul A, Harms K. J. Org. Chem. 2008; 73: 5187-5190
- 281 Hilt G, Hess W, Harms K. Synthesis 2008; 75-78
- 282 Lebœuf D, Iannazzo L, Geny A, Malacria M, Vollhardt KP. C, Aubert C, Gandon V. Chem. Eur. J. 2010; 16: 8904-8913
- 283 Kim DH, Chung YK, Han JW. Bull. Korean Chem. Soc. 2008; 29: 1224-1228
-
284 Geny A, Gaudrel S, Slowinski F, Amatore M, Chouraqui G, Malacria M, Aubert C, Gandon V. Adv. Synth. Catal. 2009; 351: 271-275
- 285 Kögl M, Brecker L, Warrass R, Mulzer J. Eur. J. Org. Chem. 2008; 2714-2730
- 286 Dahy AA, Yamada K, Koga N. Organometallics 2009; 28: 3636-3649
- 287 Dahy AA, Koga N. J. Organomet. Chem. 2010; 695: 2240-2250
- 288 Heller B, Redkin D, Gutnov A, Fischer C, Bonrath W, Karge R, Hapke M. Synthesis 2008; 69-74
- 289 Thiel I, Lamač M, Jiao H, Spannenberg A, Hapke M. Organometallics 2013; 32: 3415-3418
- 290 Thiel I, Hapke M. J. Mol. Catal. A: Chem. 2014; 383: 153-158
- 291 Sugiyama Y.-K, Okamoto S. Synthesis 2011; 2247-2254
- 292 Goswami A, Ohtaki K, Kase K, Ito T, Okamoto S. Adv. Synth. Catal. 2008; 350: 143-152
- 293 Turek P, Hocek M, Pohl R, Klepetářová B, Kotora M. Eur. J. Org. Chem. 2008; 3335-3343
- 294 Garcia P, Evanno Y, George P, Sevrin M, Ricci G, Malacria M, Aubert C, Gandon V. Org. Lett. 2011; 13: 2030-2033
- 295 Hapke M, Kral K, Fischer C, Spannenberg A, Gutnov A, Redkin D, Heller B. J. Org. Chem. 2010; 75: 3993-4003
- 296 Fischer F, Jungk P, Weding N, Spannenberg A, Ott H, Hapke M. Eur. J. Org. Chem. 2012; 5828-5838
- 297 Garcia P, Moulin S, Miclo Y, Leboeuf D, Gandon V, Aubert C, Malacria M. Chem. Eur. J. 2009; 15: 2129-2139
- 298 Meißner A, Groth U. Synlett 2010; 1051-1054
- 299 Miclo Y, Garcia P, Evanno Y, George P, Sevrin M, Malacria M, Gandon V, Aubert C. Synlett 2010; 2314-2318
- 300 Chercheja S, Klívar J, Jančařík A, Rybáček J, Salzl S, Tarábek J, Pospíšil L, Chocholoušová JV, Vacek J, Pohl R, Císařová I, Starý I, Stará IG. Chem. Eur. J. 2014; 20: 8477-8482
- 301 Kuttner JR, Warratz S, Hilt G. Synthesis 2012; 44: 1293-1303
- 302 Auvinet A.-L, Harrity JP. A, Hilt G. J. Org. Chem. 2010; 75: 3893-3896
- 303 Hilt G, Janikowski J. Org. Lett. 2009; 11: 773-776
- 304 Hilt G, Janikowski J, Schwarzer M, Burghaus O, Sakow D, Bröring M, Drüschler M, Huber B, Roling B, Harms K, Frenking G. J. Organomet. Chem. 2014; 749: 219-223
- 305 Fiebig L, Kuttner J, Hilt G, Schwarzer MC, Frenking G, Schmalz H.-G, Schäfer M. J. Org. Chem. 2013; 78: 10485-10493
- 306 Hilt G, Danz M. Synthesis 2008; 2257-2263
- 307 Erver F, Hilt G, Harms K. Synthesis 2011; 972-978
- 308 Pünner F, Schieven J, Hilt G. Org. Lett. 2013; 15: 4888-4891
- 309 Raster P, Weiss S, Hilt G, König B. Synthesis 2011; 905-908
- 310 Raster P, Schmidt A, Rambow M, Kuzmanovic N, König B, Hilt G. Chem. Commun. 2014; 50: 1864-1866
- 311 Arndt M, Hilt G, Khlebnikov AF, Kozhushkov SI, de Meijere A. Eur. J. Org. Chem. 2012; 3112-3121 Addendum, Eur. J. Org. Chem. 2013, 1171–1172
- 312 Yamakawa T, Yoshikai N. Org. Lett. 2013; 15: 196-199
- 313 Wakabayashi R, Kurahashi T, Matsubara S. Org. Lett. 2012; 14: 4794-4797
- 314 Komeyama K, Okamoto Y, Takaki K. Angew. Chem. Int. Ed. 2014; 53: 11325-11328
- 315 Pünner F, Hilt G. Chem. Commun. 2012; 48: 3617-3619
- 316 Röse P, Pünner F, Hilt G, Harms K. Synlett 2013; 24: 1101-1104
- 317 Clavier H, de Jeune K, de Riggi I, Tenaglia A, Buono G. Org. Lett. 2011; 13: 308-311
- 318 Hilt G, Paul A, Hengst C. Synthesis 2009; 3305-3310
- 319 Toselli N, Martin D, Achard M, Tenaglia A, Bürgi T, Buono G. Adv. Synth. Catal. 2008; 350: 280-286
- 320 Du P, Li H, Wang Y, Cheng J, Wan X. Org. Lett. 2014; 16: 6350-6353
- 321 Le Floch C, Le Gall E, Léonel E, Koubaa J, Martens T, Retailleau P. Eur. J. Org. Chem. 2010; 5279-5286
- 322 Le Floch C, Laymand K, Le Gall E, Léonel E. Adv. Synth. Catal. 2012; 354: 823-827
- 323 Dong Z, Liu X, Feng J, Wang M, Lin L, Feng X. Eur. J. Org. Chem. 2011; 137-142
- 324 Cao W, Liu X, Wang W, Lin L, Feng X. Org. Lett. 2011; 13: 600-603
- 325 Zhang Y, Ji J, Zhang X, Lin S, Pan Q, Jia L. Org. Lett. 2014; 16: 2130-2133
- 326 Le Gall E, Sengmany S, Samb I, Benakrour S, Colin C, Pignon A, Léonel E. Org. Biomol. Chem. 2014; 12: 3423-3426
- 327 Prieto O, Lam HW. Org. Biomol. Chem. 2008; 6: 55-57
- 328 Rudkin ME, Joensuu PM, MacLachlan WS, Lam HW. Org. Lett. 2008; 10: 2939-2942
- 329 Lumby RJ. R, Joensuu PM, Lam HW. Tetrahedron 2008; 64: 7729-7740
- 330 Karmakar A, Maji T, Wittmann S, Reiser O. Chem. Eur. J. 2011; 17: 11024-11029
- 331 Park J, Lang K, Abboud KA, Hong S. J. Am. Chem. Soc. 2008; 130: 16484-16485
- 332 Lang K, Park J, Hong S. Angew. Chem. Int. Ed. 2012; 51: 1620-1624
- 333 Chen Z, Furutachi M, Kato Y, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2009; 48: 2218-2220
- 334 Furutachi M, Chen Z, Matsunaga S, Shibasaki M. Molecules 2010; 15: 532-544
- 335 Kawatsura M, Hayashi S, Komatsu Y, Hayase S, Itoh T. Chem. Lett. 2010; 39: 466-467
- 336 Obligacion JV, Semproni SP, Chirik PJ. J. Am. Chem. Soc. 2014; 136: 4133-4136
- 337 Ertürk E, Demir AS. Tetrahedron 2008; 64: 7555-7560
- 338 Jiang Q, Sheng W, Tian M, Tang J, Guo C. Eur. J. Org. Chem. 2013; 1861-1866
- 339 Hilt G, Hengst C, Arndt M. Synthesis 2009; 395-398