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Cazin, C.  et al.: 2018 Science of Synthesis, 2016/5b: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2 DOI: 10.1055/sos-SD-224-00223
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.8 Recent Advances in N-Heterocyclic Carbene Organocatalysis

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Buch

Herausgeber: Cazin, C. ; Nolan, S.

Autoren: Basle, O.; Broggi, J.; Claver, C.; Clavier, H.; Collins, S. K.; Costabile, C.; Crevisy, C.; Crozet, D.; Davies, A.; Diesendruck, C. E.; Felten, S.; Godard, C.; Grela, K.; Holtz-Mulholland, M.; Jana, A.; Johnson, J.; Lapkin, A.; Liu, J.; Lombardía, A.; Louie, J.; Malecki, P.; Mauduit, M.; Munz, D.; Nelson, D.; Peñafiel, I.; Schmid, T.; Slugovc, C.; Smith, A. D.; Thieuleux, C.; Zhong, Y.

Titel: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

Print ISBN: 9783132414006; Online ISBN: 9783132414044; Buch-DOI: 10.1055/b-004-140260

1st edition © 2018 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

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Abstract

In recent years, organocatalysis has seen a rapid rise in popularity and this has led to a subsequent increase in the research output of the area, with organocatalysis by N-heterocyclic carbenes (NHCs) playing a significant role. Beginning with the benzoin condensation, through the work of Breslow and others to modern, asymmetric protocols, NHC organocatalysis has a rich history, which has been covered in many reviews. The focus of this chapter is on recent advances within the area of NHC organocatalysis, offering a brief historical perspective and highlighting what the authors believe to be some of the key advances made within recent times, both in terms of novel processes and significant advancements on previously documented reactions.

Schlüsselwörter

organocatalysis - organocatalysis - N-heterocyclic carbenes - azolium enolates - acyl azoliums - acyl anions - Breslow intermediate
 
  • 1 Marion N, Díez-González S, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
  • 2 Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
  • 3 Hopkinson MN, Richter C, Schedler M, Glorius F. Nature (London) 2014; 510: 485
  • 4 Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem. Rev. 2015; 115: 9307
  • 5 Douglas J, Churchill G, Smith AD. Synthesis 2012; 44: 2295
  • 6 Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
  • 7 Menon RS, Biju AT, Nair V. Chem. Soc. Rev. 2015; 44: 5040
  • 8 Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
  • 9 Seebach D. Angew. Chem. Int. Ed. Engl. 1979; 18: 239
  • 10 Wöhler F, Liebig J. Ann. Pharm. (Lemgo, Ger.) 1832; 3: 249
  • 11 Ukai T, Tanaka R, Dokawa T. J. Pharm. Soc. Jpn. 1943; 63: 296
  • 12 Lapworth A. J. Chem. Soc., Trans. 1903; 83: 995
  • 13 Breslow R. J. Am. Chem. Soc. 1958; 80: 3719
  • 14 Izquierdo J, Hutson GE, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686
  • 15 Sheehan JC, Hunneman DH. J. Am. Chem. Soc. 1966; 88: 3666
  • 16 Baragwanath L, Rose CA, Zeitler K, Connon SJ. J. Org. Chem. 2009; 74: 9214
  • 17 Sheehan JC, Hara T. J. Org. Chem. 1974; 39: 1196
  • 18 Enders D, Breuer K, Runsink J, Teles JH. Helv. Chim. Acta 1996; 79: 1899
  • 19 Knight RL, Leeper FJ. J. Chem. Soc., Perkin Trans. 1 1998; 1891
  • 20 Enders D, Kallfass U. Angew. Chem. Int. Ed. 2002; 41: 1743
  • 21 Stetter H, Dämbkes G. Synthesis 1977; 403
  • 22 Jin MY, Kim SM, Han H, Ryu DH, Yang JW. Org. Lett. 2011; 13: 880
  • 23 Jin MY, Kim SM, Mao H, Ryu DH, Song CE, Yang JW. Org. Biomol. Chem. 2014; 12: 1547
  • 24 Enders D, Niemeier O, Balensiefer T. Angew. Chem. Int. Ed. 2006; 45: 1463
  • 25 Enders D, Niemeier O, Raabe G. Synlett 2006; 2431
  • 26 Hachisu Y, Bode JW, Suzuki K. J. Am. Chem. Soc. 2003; 125: 8432
  • 27 Takikawa H, Hachisu Y, Bode JW, Suzuki K. Angew. Chem. Int. Ed. 2006; 45: 3492
  • 28 Ema T, Oue Y, Akihara K, Miyazaki Y, Sakai T. Org. Lett. 2009; 11: 4866
  • 29 Li Y, Feng Z, You S.-L. Chem. Commun. (Cambridge) 2008; 2263
  • 30 Enders D, Grossmann A, Fronert J, Raabe G. Chem. Commun. (Cambridge) 2010; 46: 6282
  • 31 Rose CA, Gundala S, Fagan C.-L, Franz JF, Connon SJ, Zeitler K. Chem. Sci. 2012; 3: 735
  • 32 Thai K, Langdon SM, Bilodeau F, Gravel M. Org. Lett. 2013; 15: 2214
  • 33 Castells J, López-Calahorra F, Bassedas M, Urrios P. Synthesis 1988; 314
  • 34 Murry JA, Frantz DE, Soheili A, Tillyer R, Grabowski EJJ, Reider PJ. J. Am. Chem. Soc. 2001; 123: 9696
  • 35 Mennen SM, Gipson JD, Kim YR, Miller SJ. J. Am. Chem. Soc. 2005; 127: 1654
  • 36 DiRocco DA, Rovis T. Angew. Chem. Int. Ed. 2012; 51: 5904
  • 37 Matsumoto T, Ohishi M, Inoue S. J. Org. Chem. 1985; 50: 603
  • 38 Mennen SM, Miller SJ. J. Org. Chem. 2007; 72: 5260
  • 39 Piel I, Pawelczyk MD, Hirano K, Fröhlich R, Glorius F. Eur. J. Org. Chem. 2011; 5475
  • 40 OʼToole SE, Rose CA, Gundala S, Zeitler K, Connon SJ. J. Org. Chem. 2011; 76: 347
  • 41 Langdon SM, Wilde MMD, Thai K, Gravel M. J. Am. Chem. Soc. 2014; 136: 7539
  • 42 Langdon SM, Legault CY, Gravel M. J. Org. Chem. 2015; 80: 3597
  • 43 Stetter H, Schreckenberg M. Angew. Chem. Int. Ed. Engl. 1973; 12: 81
  • 44 Stetter H, Kuhlmann H. Angew. Chem. Int. Ed. Engl. 1974; 13: 539
  • 45 Enders D, In Stereoselective Synthesis. Ottow E, Schöllkopf K, Schulz B.-G, Eds.;. Springer Heidelberg 1993);; p 63
    Google Scholar
  • 46 Liu Q, Perreault S, Rovis T. J. Am. Chem. Soc. 2008; 130: 14066
  • 47 Enders D, Han J, Henseler A. Chem. Commun. (Cambridge) 2008; 3989
  • 48 Zhang J, Xing C, Tiwari B, Chi YR. J. Am. Chem. Soc. 2013; 135: 8113
  • 49 Wilde MMD, Gravel M. Angew. Chem. Int. Ed. 2013; 52: 12651
  • 50 Lavallo V, Canac Y, Donnadieu B, Schoeller WW, Bertrand G. Science (Washington, D. C.) 2006; 312: 722
  • 51 Yoshida Z.-I, Tawara Y. J. Am. Chem. Soc. 1971; 93: 2573
  • 52 Yoshida Z.-I, Konishi H, Kamitori Y, Ogoshi H. Chem. Lett. 1977; 1341
  • 53 Holschumacher D, Hrib CG, Jones PG, Tamm M. Chem. Commun. (Cambridge) 2007; 3661
  • 54 Wilde MMD, Gravel M. Org. Lett. 2014; 16: 5308
  • 55 Ramanjaneyulu BT, Mahesh S, Anand RV. Org. Lett. 2015; 17: 3952
  • 56 Willis MC. Chem. Rev. 2010; 110: 725
  • 57 He J, Zheng J, Liu J, She X, Pan X. Org. Lett. 2006; 8: 4637
  • 58 He J, Tang S, Liu J, Su Y, Pan X, She X. Tetrahedron 2008; 64: 8797
  • 59 Hirano K, Biju AT, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 14190
  • 60 Piel I, Steinmetz M, Hirano K, Fröhlich R, Grimme S, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 4983
  • 61 Biju AT, Wurz NE, Glorius F. J. Am. Chem. Soc. 2010; 132: 5970
  • 62 Biju AT, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 9761
  • 63 Bugaut X, Liu F, Glorius F. J. Am. Chem. Soc. 2011; 133: 8130
  • 64 Liu F, Bugaut X, Schedler M, Fröhlich R, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 12626
  • 65 Schedler M, Wang D.-S, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 2585
  • 66 Fischer C, Smith SW, Powell DA, Fu GC. J. Am. Chem. Soc. 2006; 128: 1472
  • 67 Singh P, Singh S, Rai VK, Yadav LDS. Synlett 2010; 2649
  • 68 Padmanaban M, Biju AT, Glorius F. Org. Lett. 2011; 13: 98
  • 69 Toh QY, McNally A, Vera S, Erdmann N, Gaunt MJ. J. Am. Chem. Soc. 2013; 135: 3772
  • 70 Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
  • 71 Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
  • 72 Kang S.-K, Lee H.-W, Jang S.-B, Ho P.-S. J. Org. Chem. 1996; 61: 4720
  • 73 DiRocco DA, Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
  • 74 Jordan F, Kudzin ZH, Rios CB. J. Am. Chem. Soc. 1987; 109: 4415
  • 75 Maji B, Mayr H. Angew. Chem. Int. Ed. 2012; 51: 10408
  • 76 Collett CJ, Massey RS, Maguire OR, Batsanov AS, OʼDonoghue AC, Smith AD. Chem. Sci. 2013; 4: 1514
  • 77 DiRocco DA, Oberg KM, Rovis T. J. Am. Chem. Soc. 2012; 134: 6143
  • 78 Maji B, Horn M, Mayr H. Angew. Chem. Int. Ed. 2012; 51: 6231
  • 79 Berkessel A, Elfert S, Yatham VR, Neudörfl J.-M, Schlörer NE, Teles JH. Angew. Chem. Int. Ed. 2012; 51: 12370
  • 80 Collett CJ, Massey RS, Taylor JE, Maguire OR, OʼDonoghue AC, Smith AD. Angew. Chem. Int. Ed. 2015; 54: 6887
  • 81 Nickon A, Lambert JLSJ. J. Am. Chem. Soc. 1962; 84: 4604
  • 82 Evans DA, Andrews GC, Buckwalter B. J. Am. Chem. Soc. 1974; 96: 5560
  • 83 Nakamura E, Oshino H, Kuwajima I. J. Am. Chem. Soc. 1986; 108: 3745
  • 84 Sohn SS, Rosen EL, Bode JW. J. Am. Chem. Soc. 2004; 126: 14370
  • 85 Burstein C, Glorius F. Angew. Chem. Int. Ed. 2004; 43: 6205
  • 86 Dugal-Tessier J, OʼBryan EA, Schroeder TBH, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 4963
  • 87 Goodman CG, Walker MM, Johnson JS. J. Am. Chem. Soc. 2015; 137: 122
  • 88 Goodman CG, Johnson JS. J. Am. Chem. Soc. 2014; 136: 14698
  • 89 Corbett MT, Johnson JS. Angew. Chem. Int. Ed. 2014; 53: 255
  • 90 Wu Z, Li F, Wang J. Angew. Chem. Int. Ed. 2015; 54: 1629
  • 91 Maji B, Ji L, Wang S, Vedachalam S, Ganguly R, Liu X.-W. Angew. Chem. Int. Ed. 2012; 51: 8276
  • 92 White NA, DiRocco DA, Rovis T. J. Am. Chem. Soc. 2013; 135: 8504
  • 93 Nair V, Vellalath S, Poonoth M, Suresh E. J. Am. Chem. Soc. 2006; 128: 8736
  • 94 Chiang P.-C, Kaeobamrung J, Bode JW. J. Am. Chem. Soc. 2007; 129: 3520
  • 95 Domingo LR, Zaragoza RJ, Arno M. Org. Biomol. Chem. 2010; 8: 4884
  • 96 Izquierdo J, Orue A, Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
  • 97 Walia JS, Rao DH, Singh M. Indian J. Chem. 1964; 2: 437
  • 98 Walia JS, Rao DH, Singh M, Nath GR. Chem. Ind. (London) 1967; 583
  • 99 Sohn SS, Bode JW. Org. Lett. 2005; 7: 3873
  • 100 Chan A, Scheidt KA. Org. Lett. 2005; 7: 905
  • 101 Wang MH, Cohen DT, Schwamb CB, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2015; 137: 5891
  • 102 Fu Z, Xu J, Zhu T, Leong WWY, Chi YR. Nat. Chem. 2013; 5: 835
  • 103 Fu Z, Jiang K, Zhu T, Torres J, Chi YR. Angew. Chem. Int. Ed. 2014; 53: 6506
  • 104 Jin Z, Chen S, Wang Y, Zheng P, Yang S, Chi YR. Angew. Chem. Int. Ed. 2014; 53: 13506
  • 105 Gaunt MJ, Johansson CCC. Chem. Rev. 2007; 107: 5596
  • 106 Morrill LC, Smith AD. Chem. Soc. Rev. 2014; 43: 6214
  • 107 Reynolds NT, Rovis T. J. Am. Chem. Soc. 2005; 127: 16406
  • 108 Chow KY.-K, Bode JW. J. Am. Chem. Soc. 2004; 126: 8126
  • 109 Reynolds NT, Read de Alaniz J, Rovis T. J. Am. Chem. Soc. 2004; 126: 9518
  • 110 He M, Uc GJ, Bode JW. J. Am. Chem. Soc. 2006; 128: 15088
  • 111 He M, Beahm BJ, Bode JW. Org. Lett. 2008; 10: 3817
  • 112 Kawanaka Y, Phillips EM, Scheidt KA. J. Am. Chem. Soc. 2009; 131: 18028
  • 113 Davies AT, Taylor JE, Douglas J, Collett CJ, Morrill LC, Fallan C, Slawin AMZ, Churchill G, Smith AD. J. Org. Chem. 2013; 78: 9243
  • 114 Taylor JE, Daniels DSB, Smith AD. Org. Lett. 2013; 15: 6058
  • 115 Davies AT, Pickett PM, Slawin AMZ, Smith AD. ACS Catal. 2014; 4: 2696
  • 116 Duguet N, Campbell CD, Slawin AMZ, Smith AD. Org. Biomol. Chem. 2008; 6: 1108
  • 117 Zhang Y.-R, He L, Wu X, Shao P.-L, Ye S. Org. Lett. 2008; 10: 277
  • 118 He L, Lv H, Zhang Y.-R, Ye S. J. Org. Chem. 2008; 73: 8101
  • 119 Wang X.-N, Shao P.-L, Lv H, Ye S. Org. Lett. 2009; 11: 4029
  • 120 Wang X.-N, Zhang Y.-Y, Ye S. Adv. Synth. Catal. 2010; 352: 1892
  • 121 Huang X.-L, Chen X.-Y, Ye S. J. Org. Chem. 2009; 74: 7585
  • 122 Wang T, Huang X.-L, Ye S. Org. Biomol. Chem. 2010; 8: 5007
  • 123 Jian T.-Y, He L, Tang C, Ye S. Angew. Chem. Int. Ed. 2011; 50: 9104
  • 124 Shao P.-L, Chen X.-Y, Ye S. Angew. Chem. Int. Ed. 2010; 49: 8412
  • 125 Huang X.-L, He L, Shao P.-L, Ye S. Angew. Chem. Int. Ed. 2009; 48: 192
  • 126 Zhang Y.-R, Lv H, Zhou D, Ye S. Chem.–Eur. J. 2008; 14: 8473
  • 127 Lv H, Chen X.-Y, Sun L.-H, Ye S. J. Org. Chem. 2010; 75: 6973
  • 128 Jian T.-Y, Shao P.-L, Ye S. Chem. Commun. (Cambridge) 2011; 47: 2381
  • 129 Lv H, You L, Ye S. Adv. Synth. Catal. 2009; 351: 2822
  • 130 Wang X.-N, Lv H, Huang X.-L, Ye S. Org. Biomol. Chem. 2009; 7: 346
  • 131 Concellón C, Duguet N, Smith AD. Adv. Synth. Catal. 2009; 351: 3001
  • 132 Douglas J, Ling KB, Concellón C, Churchill G, Slawin AMZ, Smith AD. Eur. J. Org. Chem. 2010; 5863
  • 133 He M, Struble JR, Bode JW. J. Am. Chem. Soc. 2006; 128: 8418
  • 134 Kaeobamrung J, Kozlowski MC, Bode JW. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 20661
  • 135 Phillips EM, Roberts JM, Scheidt KA. Org. Lett. 2010; 12: 2830
  • 136 Hao L, Du Y, Lv H, Chen X, Jiang H, Shao Y, Chi YR. Org. Lett. 2012; 14: 2154
  • 137 Chen S, Hao L, Zhang Y, Tiwari B, Chi YR. Org. Lett. 2013; 15: 5822
  • 138 Hao L, Chen S, Xu J, Tiwari B, Fu Z, Li T, Lim J, Chi YR. Org. Lett. 2013; 15: 4956
  • 139 Cheng J, Huang Z, Chi YR. Angew. Chem. Int. Ed. 2013; 52: 8592
  • 140 Xu J, Jin Z, Chi YR. Org. Lett. 2013; 15: 5028
  • 141 Cortez GS, Tennyson RL, Romo D. J. Am. Chem. Soc. 2001; 123: 7945
  • 142 Belmessieri D, Morrill LC, Simal C, Slawin AMZ, Smith AD. J. Am. Chem. Soc. 2011; 133: 2714
  • 143 Lee A, Younai A, Price CK, Izquierdo J, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2014; 136: 10589
  • 144 Xie Y, Yu C, Li T, Tu S, Yao C. Chem.–Eur. J. 2015; 21: 5355
  • 145 Zhao X, Ruhl KE, Rovis T. Angew. Chem. Int. Ed. 2012; 51: 12330
  • 146 Mo J, Yang R, Chen X, Tiwari B, Chi YR. Org. Lett. 2013; 15: 50
  • 147 Li F, Wu Z, Wang J. Angew. Chem. Int. Ed. 2015; 54: 656
  • 148 Dong X, Yang W, Hu W, Sun J. Angew. Chem. Int. Ed. 2015; 54: 660
  • 149 Allen SE, Mahatthananchai J, Bode JW, Kozlowski MC. J. Am. Chem. Soc. 2012; 134: 12098
  • 150 Mahatthananchai J, Bode JW. Chem. Sci. 2012; 3: 192
  • 151 Shen L.-T, Shao P.-L, Ye S. Adv. Synth. Catal. 2011; 353: 1943
  • 152 Mo J, Chen X, Chi YR. J. Am. Chem. Soc. 2012; 134: 8810
  • 153 De Sarkar S, Studer A. Angew. Chem. Int. Ed. 2010; 49: 9266
  • 154 Chen X, Yang S, Song B.-A, Chi YR. Angew. Chem. Int. Ed. 2013; 52: 11134
  • 155 Huffman MA, Liebeskind LS. J. Am. Chem. Soc. 1993; 115: 4895
  • 156 Kondo T, Taguchi Y, Kaneko Y, Niimi M, Mitsudo T.-A. Angew. Chem. Int. Ed. 2004; 43: 5369
  • 157 Souillart L, Cramer N. Chem. Rev. 2015; 115: 9410
  • 158 Li B.-S, Wang Y, Jin Z, Zheng P, Ganguly R, Chi YR. Nat. Commun. 2015; 6: 6207
  • 159 Castells J, Llitjos H, Moreno-Mañas M. Tetrahedron Lett. 1977; 205
  • 160 Inoue H, Higashiura K. J. Chem. Soc., Chem. Commun. 1980; 549
  • 161 Maki BE, Chan A, Phillips EM, Scheidt KA. Org. Lett. 2007; 9: 371
  • 162 Maki BE, Scheidt KA. Org. Lett. 2008; 10: 4331
  • 163 Grasa GA, Kissling RM, Nolan SP. Org. Lett. 2002; 4: 3583
  • 164 Nyce GW, Lamboy JA, Connor EF, Waymouth RM, Hedrick JL. Org. Lett. 2002; 4: 3587
  • 165 Connor EF, Nyce GW, Myers M, Möck A, Hedrick JL. J. Am. Chem. Soc. 2002; 124: 914
  • 166 Lai C.-L, Lee HM, Hu C.-H. Tetrahedron Lett. 2005; 46: 6265
  • 167 Suzuki Y, Yamauchi K, Muramatsu K, Sato M. Chem. Commun. (Cambridge) 2004; 2770
  • 168 Kano T, Sasaki K, Maruoka K. Org. Lett. 2005; 7: 1347
  • 169 Ling KB, Smith AD. Chem. Commun. (Cambridge) 2011; 47: 373
  • 170 Lu S, Poh SB, Zhao Y. Angew. Chem. Int. Ed. 2014; 53: 11041
  • 171 Vora HU, Rovis T. J. Am. Chem. Soc. 2007; 129: 13796
  • 172 Khaleeli N, Li R, Townsend CA. J. Am. Chem. Soc. 1999; 121: 9223
  • 173 Zeitler K. Org. Lett. 2006; 8: 637
  • 174 Sun F.-G, Sun L.-H, Ye S. Adv. Synth. Catal. 2011; 353: 3134
  • 175 Chen X.-Y, Gao Z.-H, Song C.-Y, Zhang C.-L, Wang Z.-X, Ye S. Angew. Chem. Int. Ed. 2014; 53: 11611
  • 176 Du D, Hu Z, Jin J, Lu Y, Tang W, Wang B, Lu T. Org. Lett. 2012; 14: 1274
  • 177 Ni Q, Song X, Raabe G, Enders D. Chem.–Asian J. 2014; 9: 1535
  • 178 Yetra SR, Kaicharla T, Kunte SS, Gonnade RG, Biju AT. Org. Lett. 2013; 15: 5202
  • 179 Ryan SJ, Candish L, Lupton DW. J. Am. Chem. Soc. 2009; 131: 14176
  • 180 Ryan SJ, Candish L, Lupton DW. J. Am. Chem. Soc. 2011; 133: 4694
  • 181 Ryan SJ, Stasch A, Paddon-Row MN, Lupton DW. J. Org. Chem. 2012; 77: 1113
  • 182 Candish L, Levens A, Lupton DW. J. Am. Chem. Soc. 2014; 136: 14397
  • 183 Candish L, Levens A, Lupton DW. Chem. Sci. 2015; 6: 2366
  • 184 Mo J, Shen L, Chi YR. Angew. Chem. Int. Ed. 2013; 52: 8588
  • 185 Kaeobamrung J, Mahatthananchai J, Zheng P, Bode JW. J. Am. Chem. Soc. 2010; 132: 8810
  • 186 Zhu Z.-Q, Xiao J.-C. Adv. Synth. Catal. 2010; 352: 2455
  • 187 Zhu Z.-Q, Zheng X.-L, Jiang N.-F, Wan X, Xiao J.-C. Chem. Commun. (Cambridge) 2011; 47: 8670
  • 188 Zhao Y.-M, Tam Y, Wang Y.-J, Li Z, Sun J. Org. Lett. 2012; 14: 1398
  • 189 Qi J, Xie X, Han R, Ma D, Yang J, She X. Chem.–Eur. J. 2013; 19: 4146
  • 190 Lee A, Scheidt KA. Angew. Chem. Int. Ed. 2014; 53: 7594
  • 191 ElSohly AM, Wespe DA, Poore TJ, Snyder SA. Angew. Chem. Int. Ed. 2013; 52: 5789
  • 192 Guin J, De Sarkar S, Grimme S, Studer A. Angew. Chem. Int. Ed. 2008; 47: 8727
  • 193 Sarkar SD, Grimme S, Studer A. J. Am. Chem. Soc. 2010; 132: 1190
  • 194 Delany EG, Fagan C.-L, Gundala S, Mari A, Broja T, Zeitler K, Connon SJ. Chem. Commun. (Cambridge) 2013; 49: 6510
  • 195 Finney EE, Ogawa KA, Boydston AJ. J. Am. Chem. Soc. 2012; 134: 12374
  • 196 White NA, Rovis T. J. Am. Chem. Soc. 2014; 136: 14674
  • 197 Zhang Y, Du Y, Huang Z, Xu J, Wu X, Wang Y, Wang M, Yang S, Webster RD, Chi YR. J. Am. Chem. Soc. 2015; 137: 2416
  • 198 White NA, Rovis T. J. Am. Chem. Soc. 2015; 137: 10112
  • 199 Du Y, Wang Y, Li X, Shao Y, Li G, Webster RD, Chi YR. Org. Lett. 2014; 16: 5678
  • 200 Candish L, Lupton DW. Org. Biomol. Chem. 2011; 9: 8182
  • 201 Candish L, Lupton DW. J. Am. Chem. Soc. 2013; 135: 58
  • 202 Candish L, Forsyth CM, Lupton DW. Angew. Chem. Int. Ed. 2013; 52: 9149
  • 203 Kowalczyk M, Lupton DW. Angew. Chem. Int. Ed. 2014; 53: 5314
  • 204 Lee K.-S, Zhugralin AR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 7253
  • 205 Kleeberg C, Crawford AG, Batsanov AS, Hodgkinson P, Apperley DC, Cheung MS, Lin Z, Marder TB. J. Org. Chem. 2012; 77: 785
  • 206 Wu H, Radomkit S, OʼBrien JM, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 8277
  • 207 Wen K, Chen J, Gao F, Bhadury PS, Fan E, Sun Z. Org. Biomol. Chem. 2013; 11: 6350
  • 208 OʼBrien JM, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 7712
  • 209 Blanc R, Commeiras L, Parrain J.-L. Adv. Synth. Catal. 2010; 352: 661
  • 210 Wu H, Garcia JM, Haeffner F, Radomkit S, Zhugralin AR, Hoveyda AH. J. Am. Chem. Soc. 2015; 137: 10585
  • 211 Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
  • 212 He L, Jian T.-Y, Ye S. J. Org. Chem. 2007; 72: 7466
  • 213 Atienza RL, Scheidt KA. Aust. J. Chem. 2011; 64: 1158
  • 214 Chen X.-Y, Sun L.-H, Ye S. Chem.–Eur. J. 2013; 19: 4441
  • 215 Atienza RL, Roth HS, Scheidt KA. Chem. Sci. 2011; 2: 1772
  • 216 Matsuoka S.-I, Ota Y, Washio A, Katada A, Ichioka K, Takagi K, Suzuki M. Org. Lett. 2011; 13: 3722
  • 217 Biju AT, Padmanaban M, Wurz NE, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 8412
  • 218 Fèvre M, Pinaud J, Gnanou Y, Vignolle J, Taton D. Chem. Soc. Rev. 2013; 42: 2142
  • 219 Chen X.-Y, Ye S. Org. Biomol. Chem. 2013; 11: 7991
  • 220 Simonovic S, Frison J.-C, Koyuncu H, Whitwood AC, Douthwaite RE. Org. Lett. 2009; 11: 245
  • 221 Jin Z, Xu J, Yang S, Song B.-A, Chi YR. Angew. Chem. Int. Ed. 2013; 52: 12354
  • 222 Massey RS, Collett CJ, Lindsay AG, Smith AD, OʼDonoghue AC. J. Am. Chem. Soc. 2012; 134: 20421