RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(13): 1939-1973
DOI: 10.1055/s-0035-1560444
DOI: 10.1055/s-0035-1560444
review
Recent Advances in the Synthesis of Sulfones
Weitere Informationen
Publikationsverlauf
Received: 04. März 2016
Accepted after revision: 04. April 2016
Publikationsdatum:
07. Juni 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201613/lookinside/thumbnails/ss-2016-e0158-r_10-1055_s-0035-1560444-1.jpg)
Abstract
Sulfones are versatile intermediates in organic synthesis and important building blocks in the construction of biological active molecules or functional materials. This review provides a summary of recent developments in the synthesis of sulfones.
1 Introduction
2 Classical Methods and Variants
2.1 Oxidation of Sulfides
2.2 Aromatic Sulfonylation
2.3 Alkylation/Arylation of Sulfinates
2.4 Addition to Alkenes and Alkynes
2.5 Miscellaneous Methods
3 Metal-Catalyzed Coupling Reactions
4 Sulfone Synthesis by C–H Functionalization
5 Sulfur Dioxide Based Three-Component Approaches
6 Biological Synthesis of Sulfones
7 Conclusion
-
References
- 1a Whitham GH. Organosulfur Chemistry . Oxford University Press; Oxford/New York: 1995
- 1b Oae S. Organic Chemistry of Sulfur . Plenium Press; New York: 1977
- 1c Stirling CJ. M. Organic sulphur chemistry: Structure, mechanism, and synthesis . Butterworths; London/Boston: 1975
- 1d Patai S, Rappoport Z, Stirling CJ. M. The Chemistry of Sulphones and Sulphoxides . Wiley; New York: 1988
-
2 Trost BM, Chadiri MR. J. Am. Chem. Soc. 1984; 106: 7260
- 4a Alonso DA, Ájera CN. Org. React. 2009; 72: 367
- 4b Gui J, Zhou Q, Pan C.-M, Yabe Y, Burns AC, Collins MR, Ornelas MA, Ishihara Y, Baran PS. J. Am. Chem. Soc. 2014; 136: 4853
- 4c Ku Y.-Y, Patel RR, Roden BA, Sawick DP. Tetrahedron Lett. 1994; 35: 6017
- 4d Brown AC, Carpino LA. J. Org. Chem. 1985; 50: 1749
- 4e Kumar V, Ramesh NG. Chem. Commun. 2006; 4952
- 4f Abrunhosa I, Gulea M, Masson S. Synthesis 2004; 928
- 6a Ramberg L, Bäcklund B. Ark. Chim., Mineral Geol. 1940; 27: 1
- 6b Taylor RJ. K, Casy G. Org. React. 2004; 62: 359
- 7a Julia M, Paris J.-M. Tetrahedron Lett. 1973; 14: 4833
- 7b Kocienski PJ, Lythgoe B, Ruston S. J. Chem. Soc., Perkin Trans. 1 1978; 829
- 7c Aïssa C. J. Org. Chem. 2006; 71: 360
- 7d Blakemore PR. J. Chem. Soc., Perkin Trans. 1 2002; 2563
- 8a Li JJ. Name Reactions in Heterocyclic Chemistry . John Wiley & Sons; Hoboken: 2005
- 8b van Leusen AM, Hoogenboom BE, Siderius H. Tetrahedron Lett. 1972; 13: 2369
- 8c van Leusen AM, Wildeman J, Oldenziel OH. J. Org. Chem. 1977; 42: 1153
- 9 Swenson RE, Sowin TJ, Zhang HQ. J. Org. Chem. 2002; 67: 9182
- 10a Acton QA. Sulfones—Advances in Research and Application . Scholarly Editions; Atlanta: 2013
- 10b Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
- 10c Bisseret P, Blanchard N. Org. Biomol. Chem. 2013; 11: 5393
- 11a Goadsby PJ, Ferrari MD, Olesen J, Stovner LJ, Senard JM, Jackson NC, Poole PH. Neurology 2000; 54: 156
- 11b Sandrini G, Farkkila M, Burgess G, Forster E, Haughie S. Neurology 2002; 59: 1210
- 12a Iversen P, Tyrrell CJ, Kaisary AV, Anderson JB, van Poppel H, Tammela TL, Chamberlain M, Carroll K, Melezinek I. J. Urol. 2000; 164: 1579
- 12b Le Y, Ji H, Chen J.-F, Shen Z, Yun J, Pu M. Int. J. Pharm. 2009; 370: 175
- 12c Kanfer I. J. Pharm. Pharm. Sci. 2000; 5: 1
- 13a Yazdanyar S, Boer J, Ingvarsson G, Szepietowski JC, Jemec GB. E. Dermatology 2011; 222: 342
- 13b Lopez de Compadre Rosa L, Pearlstein RA, Hopfinger AJ, Seydel JK. J. Med. Chem. 1987; 30: 900
- 13c Zhang F.-R, Liu H, Irwanto A, Fu X.-A, Li Y, Yu G.-Q, Yu Y.-X, Chen M.-F, Low H.-Q, Li J.-H, Bao F.-F, Foo J.-N, Bei J.-X, Jia X.-M, Liu J, Liany H, Wang N, Niu G.-Y, Wang Z.-Z, Shi B.-Q, Tian H.-Q, Liu H.-X, Ma S.-S, Zhou Y, You J.-B, Yang Q, Wang C, Chu T.-S, Liu D.-C, Yu X.-L, Sun Y.-H, Ning Y, Wei Z.-H, Chen S.-L, Chen X.-C, Zhang Z.-X, Liu Y.-X, Pulit SL, Wu W.-B, Zheng Z.-Y, Yang R.-D, Long H, Liu Z.-S, Wang J.-Q, Li M, Zhang L.-H, Wang H, Wang L.-M, Xiao P, Li J.-L, Huang Z.-M, Huang J.-X, Li Z, Xiong L, Yang J, Wang X.-D, Yu D.-B, Lu X.-M, Zhou G.-Z, Yan L.-B, Shen J.-P, Zhang G.-C, Zeng Y.-X, de Bakker P, Chen S.-M, Liu J.-J. N. Engl. J. Med. 2013; 369: 1620
- 14a Mitchell G, Bartlett DW, Fraser TE. M, Hawkes TR, Holt DC, Townson JK, Wichert RA. Pest. Manag. Sci. 2001; 57: 120
- 14b Beaudegnies R, Edmunds AJ. F, Fraser TE. M, Hall RG, Hawkes TR, Mitchell G, Schaetzer J, Wendeborn S, Wibley J. Bioorg. Med. Chem. 2009; 17: 4134
- 15 Tanetani Y, Kaku K, Kawai K, Fujioka T, Shimizu T. Pest. Biochem. Physiol. 2009; 95: 47
- 16 Takahashi H, Ohki A, Kanzaki M, Tanaka A, Sato Y, Matthes B, Böger P, Wakabayashi K. Z. Naturforsch. C 2001; 56: 781
- 17 El-Hibri MJ, Weinberg SA In Encyclopedia of Polymer Science and Technology . Mark HF. Wiley; New York: 2014: 179
- 18a Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 3121
- 18b Griffin RJ, Henderson A, Curtin NJ, Echalier A, Endicott JA, Hardcastle IR, Newell DR, Noble ME. M, Wang L.-Z, Golding BT. J. Am. Chem. Soc. 2006; 128: 6012
- 18c Catarinella M, Grüner T, Strittmatter T, Marx A, Mayer TU. Angew. Chem. Int. Ed. 2009; 48: 9072
- 18d Posner GH, Maxwell JP, O’Dowd H, Krasavin M, Xie S, Shapiro TA. Bioorg. Med. Chem. 2000; 8: 1361
- 18e Tozkoparan B, Küpeli E, Yeşilada E, Ertan M. Bioorg. Med. Chem. 2007; 15: 1808
- 19 Varma RS, Naicker KP. Org. Lett. 1999; 1: 189
- 20a Kirihara M, Itou A, Noguchi T, Yamamoto J. Synlett 2010; 1557
- 20b Bahrami K, Khodaei MM, Sheikh Arabi M. J. Org. Chem. 2010; 75: 6208
- 20c Karimi B, Ghoreishi-Nezhad M, Clark JH. Org. Lett. 2005; 7: 625
- 20d Jana NK, Verkade JG. Org. Lett. 2003; 5: 3787
- 20e Fukuda N, Ikemoto T. J. Org. Chem. 2010; 75: 4629
- 21 Shaabani A, Mirzaei P, Naderi S, Lee DG. Tetrahedron 2004; 60: 11415
- 22 Jereb M. Green Chem. 2012; 14: 3047
- 23 Olah GA. Friedel–Crafts and Related Reactions . Wiley-Interscience; New York: 1964
- 24a Jensen FR, Goldman G In Friedel–Crafts and Related Reactions . Olah GA. Wiley-Interscience; New York: 1964: 1319
- 24b Olah GA, Kobayashi S, Nishimura J. J. Am. Chem. Soc. 1973; 95: 564
- 24c Olah GA, Lin HC. Synthesis 1974; 342
- 24d Hyatt JA, White AW. Synthesis 1984; 214
- 24e Effenberger F, Huthmacher K. Angew. Chem. Int. Ed. 1974; 13: 409
- 24f Répichet S, Le Roux C, Hernandez P, Dubac J, Desmurs J.-R. J. Org. Chem. 1999; 64: 6479
- 24g Graybill BM. J. Org. Chem. 1967; 32: 2931
- 24h Sipe Jr HJ, Clary DW, White SB. Synthesis 1984; 283
- 24i Ueda M, Uchiyama K, Kano T. Synthesis 1984; 323
- 24j Effenberger F, Huthmacher K. Chem. Ber. 1976; 109: 2315
- 24k Ono M, Nakamura Y, Sato S, Itoh I. Chem. Lett. 1988; 395
- 25a Choudary BM, Chowdari N, Kantam M, Kannan R. Tetrahedron Lett. 1999; 40: 2859
- 25b Singh RP, Kamble RM, Chandra KL, Saravanan P, Singh VK. Tetrahedron 2001; 57: 241
- 25c Jang DO, Moon KS, Cho DH, Kim J.-G. Tetrahedron Lett. 2006; 47: 6063
- 25d Bahrami K, Khodei MM, Shahbazi F. Tetrahedron Lett. 2008; 49: 3931
- 25e Choudary BM, Chowdari NS, Kantam ML. J. Chem. Soc., Perkin Trans. 1 2000; 2689
- 25f Nara SJ, Harjani JR, Salunkhe MM. J. Org. Chem. 2001; 66: 8616
- 25g Noronha RG, Fernandes AC, Romão CC. Tetrahedron Lett. 2009; 50: 1407
- 25h Borujeni KP, Tamami B. Catal. Commun. 2007; 8: 1191
- 25i Marquié J, Laporterie A, Dubac J, Roques N, Desmurs J.-R. J. Org. Chem. 2001; 66: 421
- 26a Olah GA, Mathew T, Surya Prakash GK. Chem. Commun. 2001; 1696
- 26b Li H.-Z, Xiao L.-W, Li H.-Y, Wang K.-F, Li X. J. Chem. Res., Synop. 2003; 493
- 27a Mirjalali MB, Zolfigol MA, Bamoniri A, Khazdooz L. Bull. Korean Chem. Soc. 2003; 24: 1009
- 27b Alizadeh A, Khodaei MM, Nazari E. Tetrahedron Lett. 2007; 48: 6805
- 28 Rueggerberg WH. C, Sauls TW, Norwood SL. J. Org. Chem. 1955; 20: 455
- 29a Fouque G, Lacroix J. Bull. Soc. Chim. Fr. 1923; 33: 180
- 29b Kozlov VV, Vol’fson TI, Kozlova NA, Tubyarskaya GS. J. Gen. Chem. USSR 1962; 32: 3373
- 30 Joly R, Bucourt R, Mathieu J. Recl. Trav. Chim. Pays-Bas 1959; 78: 527
- 31 Yang Y, Chen Z, Rao Y. Chem. Commun. 2014; 50: 15037
- 32 Yao B, Zhang Y. Tetrahedron Lett. 2008; 49: 5385
- 33 Aziz J, Messaoudi S, Alami M, Hamze A. Org. Biomol. Chem. 2014; 12: 9743
- 34 Meek JS, Fowler JS. J. Org. Chem. 1968; 33: 3422
- 35 Oxley P, Partridge MW, Robson TD, Short WF. J. Chem. Soc. 1946; 763
- 36 Culvenor CC. J, Davies W, Heath NS. J. Chem. Soc. 1949; 278
- 37a Achmatowicz O, Michalski J. Rocz. Chem. 1956; 30: 243
- 37b Hansen OR, Hammer R, Vister T. Acta Chem. Scand. 1953; 7: 1331
- 38 Roblin RO, Williams JH, Anderson GW. J. Am. Chem. Soc. 1941; 63: 1930
- 39a Maloney KM, Kuethe JT, Linn K. Org. Lett. 2011; 13: 102
- 39b Liang S, Zhang R.-Y, Xi L.-Y, Chen S.-Y, Yu X.-Q. J. Org. Chem. 2013; 78: 11874
-
40a Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 40b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 40c Olofsson B. Arylation with Diaryliodonium Salts. In Topics in Current Chemistry . Springer; Berlin/Heidelberg: 2015: 1
- 40d Silva Jr. LF, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
- 41 Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
- 42 Pandya VG, Mhaske SB. Org. Lett. 2014; 16: 3836
- 43 Liang S, Zhang R.-Y, Wang G, Chen S.-Y, Yu X.-Q. Eur. J. Org. Chem. 2013; 7050
- 44 Chawla R, Kapoor R, Singh AK, Yadav LD. S. Green Chem. 2012; 14: 1308
- 45 Guan Z.-H, Zuo W, Zhao L.-B, Ren Z.-H, Liang Y.-M. Synthesis 2007; 1465
- 46 Reddy MA, Reddy PS, Sreedhar B. Adv. Synth. Catal. 2010; 352: 1861
- 47 Chu X.-Q, Meng H, Xu X.-P, Ji S.-J. Chem. Eur. J. 2015; 21: 11359
- 48 Liu C.-R, Li M.-B, Cheng D.-J, Yang C.-F, Tian S.-K. Org. Lett. 2009; 11: 2543
- 49a Dornow A, Bartsch W. Liebigs Ann. Chem. 1957; 602: 23
- 49b Powell BF, Overberger CG, Anselme J.-P. J. Heterocycl. Chem. 1983; 20: 121
- 49c Carter P, Stevens TS. J. Chem. Soc. 1961; 1743
- 49d Lemal DM, Rave TW, McGregor SD. J. Am. Chem. Soc. 1963; 85: 1944
- 49e Lemal DM, Menger F, Coats E. J. Am. Chem. Soc. 1964; 86: 2395
- 49f Carpino LA. Chem. Ind. 1957; 172
- 49g Carpino LA. J. Am. Chem. Soc. 1957; 79: 4427
- 49h Baker W, McOmie JF. W, Preston DR. J. Chem. Soc. 1961; 2971
- 50 Ballini R, Marcantoni E, Petrini M. Tetrahedron 1989; 45: 6791
- 51 Yang Y, Tang L, Zhang S, Guo X, Zha Z, Wang Z. Green Chem. 2014; 16: 4106
- 52 Li X, Xu X, Tang Y. Org. Biomol. Chem. 2013; 11: 1739
- 53 Song R.-J, Liu Y, Liu Y.-Y, Li J.-H. J. Org. Chem. 2011; 76: 1001
- 54 Reddy LR, Hu B, Prashad M, Prasad K. Angew. Chem. Int. Ed. 2009; 48: 172
- 55 Li H.-H, Dong D.-J, Jin Y.-H, Tian S.-K. J. Org. Chem. 2009; 74: 9501
- 56 Pan X.-Q, Zou J.-P, Yi W.-B, Zhang W. Tetrahedron 2015; 71: 7481
- 57a Asscher M, Vofsi D. J. Chem. Soc. 1964; 4962
- 57b Skell PS, Woodworth RC, McNamara JH. J. Am. Chem. Soc. 1957; 79: 1253
- 57c Cristol SJ, Davies DI. J. Org. Chem. 1964; 29: 1282
- 58a Dénès F, Pichowicz M, Povie G, Renaud P. Chem. Rev. 2014; 114: 2587
- 58b Dénès F, Schiesser CH, Renaud P. Chem. Soc. Rev. 2013; 42: 7900
- 58c Majumdar KC, Debnath P. Tetrahedron 2008; 64: 9799
- 58d Hart DJ In Radicals in Organic Synthesis . Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: 279
- 58e Bertrand MP, Ferreri C In Radicals in Organic Synthesis . Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: 485
- 58f Alfassi ZB. S-Centered Radicals . Wiley; Chichester: 1999
- 59a Quebatte L, Thommes K, Severin K. J. Am. Chem. Soc. 2006; 128: 7440
- 59b Nair RP, Kim TH, Frost BJ. Organometallics 2009; 28: 4681
- 60 Kamigata N, Shimizu T. Rev. Heteroat. Chem. 1997; 17: 1
- 61 Zeng X, Ilies L, Nakamura E. Org. Lett. 2012; 14: 954
- 62 Gilmore K, Gold B, Clark RJ, Alabugin IV. Aust. J. Chem. 2013; 66: 336
- 63a Kang S.-K, Ko B.-S, Ha Y.-H. J. Org. Chem. 2001; 66: 3630
- 63b Kang S.-K, Ko B.-S, Lee D.-M. Synth. Commun. 2006; 32: 3263
- 63c Kang S.-K, Seo H.-W, Ha Y.-H. Synthesis 2001; 1321
- 64 Kang S.-K, Ha Y.-H, Kim D.-H, Lim Y, Jung J. Chem. Commun. 2001; 1306
- 65 Alabugin IV, Timokhin VI, Abrams JN, Manoharan M, Abrams R, Ghiviriga I. J. Am. Chem. Soc. 2008; 130: 10984
- 66 Mantrand N, Renaud P. Tetrahedron 2008; 64: 11860
- 67 Taniguchi N. Synlett 2011; 1308
- 68 Taniguchi N. Tetrahedron 2014; 70: 1984
- 69 Xu Y, Zhao J, Tang X, Wu W, Jiang H. Adv. Synth. Catal. 2014; 356: 2029
- 70 Katrun P, Chiampanichayakul S, Korworapan K, Pohmakotr M, Reutrakul V, Jaipetch T, Kuhakarn C. Eur. J. Org. Chem. 2010; 5633
- 71 Wei W, Wen J, Yang D, Du J, You J, Wang H. Green Chem. 2014; 16: 2988
- 72 Xi Y, Dong B, McClain EJ, Wang Q, Gregg TL, Akhmedov NG, Petersen JL, Shi X. Angew. Chem. Int. Ed. 2014; 53: 4657
- 73 Meyer AU, Jäger S, Prasad Hari D, König B. Adv. Synth. Catal. 2015; 357: 2050
- 74 Xia D, Miao T, Li P, Wang L. Chem. Asian J. 2015; 10: 1919
- 75 Yang W, Yang S, Li P, Wang L. Chem. Commun. 2015; 51: 7520
- 76 Taniguchi N. J. Org. Chem. 2015; 80: 7797
- 77 Kariya A, Yamaguchi T, Nobuta T, Tada N, Miura T, Itoh A. RSC Adv. 2014; 4: 13191
- 78 Lu Q, Zhang J, Wei F, Qi Y, Wang H, Liu Z, Lei A. Angew. Chem. Int. Ed. 2013; 52: 7156
- 79 Singh AK, Chawla R, Yadav LD. S. Tetrahedron Lett. 2014; 55: 4742
- 80 Lu Q, Zhang J, Zhao G, Qi Y, Wang H, Lei A. J. Am. Chem. Soc. 2013; 135: 11481
- 81 Li X, Xu Y, Wu W, Jiang C, Qi C, Jiang H. Chem. Eur. J. 2014; 20: 7911
- 82 Tang S, Wu Y, Liao W, Bai R, Liu C, Lei A. Chem. Commun. 2014; 50: 4496
- 83 Sun K, Lv Y, Zhu Z, Jiang Y, Qi J, Wu H, Zhang Z, Zhang G, Wang X. RSC Adv. 2015; 5: 50701
- 84 Li X, Xu X, Shi X. Tetrahedron Lett. 2013; 54: 3071
- 85 Rong G, Mao J, Yan H, Zheng Y, Zhang G. J. Org. Chem. 2015; 80: 4697
- 86 Taniguchi T, Idota A, Ishibashi H. Org. Biomol. Chem. 2011; 9: 3151
- 87 Wei W, Liu C, Yang D, Wen J, You J, Suo Y, Wang H. Chem. Commun. 2013; 49: 10239
- 88 Xu K, Khakyzadeh V, Bury T, Breit B. J. Am. Chem. Soc. 2014; 136: 16124
- 89 Li X, Xu X, Zhou C. Chem. Commun. 2012; 48: 12240
- 90 Liu Z, Chen X, Chen J, Qu L, Xia Y, Wu H, Ma H, Zhu S, Zhao Y. RSC Adv. 2015; 5: 71215
- 91 Gao X, Pan X, Gao J, Huang H, Yuan G, Li Y. Chem. Commun. 2015; 51: 210
- 92a Chen J.-Y, Chen X.-L, Li X, Qu L.-B, Zhang Q, Duan L.-K, Xia Y.-Y, Chen X, Sun K, Liu Z.-D, Zhao Y.-F. Eur. J. Org. Chem. 2015; 314
- 92b Jiang Y, Loh T.-P. Chem. Sci. 2014; 5: 4939
- 93 Katrun P, Hlekhlai S, Meesin J, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. Org. Biomol. Chem. 2015; 13: 4785
- 94 Jiang Q, Xu B, Jia J, Zhao A, Zhao Y.-R, Li Y.-Y, He N.-N, Guo C.-C. J. Org. Chem. 2014; 79: 7372
- 95 Chen J, Mao J, Zheng Y, Liu D, Rong G, Yan H, Zhang C, Shi D. Tetrahedron 2015; 71: 5059
- 96 Gao J, Lai J, Yuan G. RSC Adv. 2015; 5: 66723
- 97 Xu Y, Tang X, Hu W, Wu W, Jiang H. Green Chem. 2014; 16: 3720
- 98 Li H.-S, Liu G. J. Org. Chem. 2014; 79: 509
- 99 Rong G, Mao J, Yan H, Zheng Y, Zhang G. J. Org. Chem. 2015; 80: 7652
- 100 Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Org. Lett. 2015; 17: 2656
- 101 Li S, Li X, Yang F, Wu Y. Org. Chem. Front. 2015; 2: 1076
- 102 Lu Q, Zhang J, Peng P, Zhang G, Huang Z, Yi H, Miller JT, Lei A. Chem. Sci. 2015; 6: 4851
- 103 Yadav VK, Srivastava VP, Yadav LD. S. Synlett 2016; 27: 427
- 104 Tang Y, Fan Y, Gao H, Li X, Xu X. Tetrahedron Lett. 2015; 56: 5616
- 105 Jiang H, Cheng Y, Zhang Y, Yu S. Eur. J. Org. Chem. 2013; 5485
- 106 Tang Y, Zhang Y, Wang K, Li X, Xu X, Du X. Org. Biomol. Chem. 2015; 13: 7084
- 107a Gilman H, Beaber NJ, Myers CH. J. Am. Chem. Soc. 1925; 47: 2047
- 107b Burton H, Davy WA. J. Chem. Soc. 1948; 528
- 107c Whitmore FC, Thurman N. J. Am. Chem. Soc. 1923; 45: 1068
- 108 Gilman H, Fothergill RE. J. Am. Chem. Soc. 1929; 51: 3501
- 109 Shirota Y, Nagai T, Tokura N. Tetrahedron 1969; 25: 3193
- 110 Katritzky AR, Abdel-Fattah AA, Vakulenko AV, Tao H. J. Org. Chem. 2005; 70: 9191
- 111a Gerasimova TN, Bushmelev VA, Koptyug VA. Russ. J. Org. Chem. 1965; 1: 1667
- 111b Bradley W, Hannon JD. Chem. Ind. 1959; 540
- 112 Mao S, Gao YR, Zhu XQ, Guo DD, Wang YQ. Org. Lett. 2015; 17: 1692
- 113 Ojha DP, Prabhu KR. Org. Lett. 2015; 17: 18
- 114 Feng XW, Wang J, Zhang J, Yang J, Wang N, Yu XQ. Org. Lett. 2010; 12: 4408
- 115 Yang Z, Hao WJ, Wang SL, Zhang JP, Jiang B, Li G, Tu SJ. J. Org. Chem. 2015; 80: 9224
- 116 Gigant N, Drège E, Retailleau P, Joseph D. Chem. Eur. J. 2015; 21: 15544
- 117 Mock WL. J. Am. Chem. Soc. 1966; 88: 2857
- 118 Smith M. March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure. Wiley; Hoboken: 2013
- 119a Deguin B, Vogel P. J. Am. Chem. Soc. 1992; 114: 9210
- 119b Vogel P, Sordo JA. Curr. Org. Chem. 2006; 10: 2007
- 119c Suarez D, Sordo TL, Sordo JA. J. Org. Chem. 1995; 60: 2848
- 119d Suarez D, Gonzalez J, Sordo TL, Sordo JA. J. Org. Chem. 1994; 59: 8058
- 119e Suarez D, Sordo TL, Sordo JA. J. Am. Chem. Soc. 1994; 116: 763
- 120 Suzuki H, Abe H. Tetrahedron Lett. 1995; 36: 6239
- 121 Zhu W, Ma D. J. Org. Chem. 2005; 70: 2696
- 122 Baskin JM, Wang Z. Org. Lett. 2002; 4: 4423
- 123 Yang M, Shen H, Li Y, Shen C, Zhang P. RSC Adv. 2014; 4: 26295
- 124 Bian M, Xu F, Ma C. Synthesis 2007; 2951
- 125 Srinivas BT. V, Rawat VS, Konda K, Sreedhar B. Adv. Synth. Catal. 2014; 356: 805
- 126 Yuan YQ, Guo SR. Synlett 2011; 2750
- 127 Gund SH, Shelkar RS, Nagarkar JM. RSC Adv. 2015; 5: 62926
- 128 Zhang K, Xu XH, Qing FL. J. Org. Chem. 2015; 80: 7658
- 129a Cacchi S, Fabrizi G, Goggiamani A, Parisi LM. Org. Lett. 2002; 4: 4719
- 129b Cacchi S, Fabrizi G, Goggiamani A, Parisi LM. Synlett 2003; 361
- 129c Cacchi S, Fabrizi G, Goggiamani A, Parisi LM, Bernini R. J. Org. Chem. 2004; 69: 5608
- 130 Reeves DC, Rodriguez S, Lee H, Haddad N, Krishnamurthy D, Senanayake CH. Tetrahedron Lett. 2009; 50: 2870
- 131 Tian H, Cao A, Qiao L, Yu A, Chang J, Wu Y. Tetrahedron 2014; 70: 9107
- 132 Beaulieu C, Guay D, Wang Z, Evans DA. Tetrahedron Lett. 2004; 45: 3233
- 133 Kir A, Sayyed IA, Lo WF, Kaiser HM, Beller M, Tse MK. Org. Lett. 2007; 9: 3405
- 134 Huang F, Batey RA. Tetrahedron 2007; 63: 7667
- 135 Kantam M, Neelima B, Sreedhar B, Chakravarti R. Synlett 2008; 1455
- 136 Yang H, Li Y, Jiang M, Wang J, Fu H. Chem. Eur. J. 2011; 17: 5652
- 137 Zhou PX, Ye YY, Zhao LB, Hou JY, Kang X, Chen DQ, Tang Q, Zhang JY, Huang QX, Zheng L, Ma JW, Xu PF, Liang YM. Chem. Eur. J. 2014; 20: 16093
- 138a Tsuji J. Acc. Chem. Res. 1969; 2: 144
-
138b Trost BM. Tetrahedron 1977; 33: 2615
-
138c Trost BM, Van Vranken DL. Chem. Rev. 1996; 96: 395
-
138d Trost BM, Crawley ML. Chem. Rev. 2003; 103: 2921
- 139a Billamboz M, Mangin F, Drillaud N, Chevrin-Villette C, Banaszak-Léonard E, Len C. J. Org. Chem. 2014; 79: 493
- 139b Inomata K, Yamamoto T, Kotake H. Chem. Lett. 1981; 1357
- 139c Felpin F.-X, Landais Y. J. Org. Chem. 2005; 70: 6441
- 139d Liao M.-C, Duan X.-H, Liang Y.-M. Tetrahedron Lett. 2005; 46: 3469
-
139e Uozumi Y, Danjo H, Hayashi T. Tetrahedron Lett. 1997; 38: 3557
-
139f Seebach D, Devaquet E, Ernst A, Hayakawa M, Kühnle FN. M, Schweizer WB, Weber B. Helv. Chim. Acta 1995; 78: 1636
- 139g Vasen D, Salzer A, Gerhards F, Gais H.-J, Bieler NH, Togni A. Organometallics 2000; 19: 539
- 139h Trost BM, Crawley ML, Lee CB. Chem. Eur. J. 2006; 12: 2171
- 139i Boldrini GP, Savoia D, Tagliavini E, Trombini C, Umani-Ronchi A. J. Organomet. Chem. 1984; 268: 97
- 140a Safi M, Sinou D. Tetrahedron Lett. 1991; 32: 2025
- 140b Kang S.-K, Park D.-C, Jeon J.-H, Rho H.-S, Yu C.-M. Tetrahedron Lett. 1994; 35: 2357
- 141a Chandrasekhar S, Jagadeshwar V, Saritha B, Narsihmulu C. J. Org. Chem. 2005; 70: 6506
- 141b Ma X.-T, Dai R.-H, Zhnag J, Gu Y, Tian S.-K. Adv. Synth. Catal. 2014; 356: 2984
-
142a Ono N, Hamamoto I, Kawai T, Kaji A, Tamura R, Kakihana M. Bull. Chem. Soc. Jpn. 1986; 59: 405
- 142b Tamura R, Kai Y, Kakihana M, Hayashi K, Tsuji M, Nakamura T, Oda D. J. Org. Chem. 1986; 51: 4375
- 143 Wu XS, Chen Y, Li MB, Zhou MG, Tian SK. J. Am. Chem. Soc. 2012; 134: 14694
- 144a Hiroi K, Kurihara Y. J. Chem. Soc., Chem. Commun. 1989; 1778
- 144b Hiroi K, Makino K. Chem. Pharm. Bull. 1988; 36: 1744
- 144c Hiroi K, Makino K. Chem. Lett. 1986; 617
- 144d Hiroi K, Kitayama R, Sato S. J. Chem. Soc., Chem. Commun. 1984; 303
- 144e Hiroi K, Kitayama R, Sato S. Chem. Pharm. Bull. 1984; 32: 2628
- 144f Hiroi K, Kitayama R, Sato S. J. Chem. Soc., Chem. Commun. 1983; 1470
-
144g Eichelmann H, Gais H.-J. Tetrahedron: Asymmetry 1995; 6: 643
- 144h Gavrilov KN, Bondarev OG, Tsarev VN, Shiryaev AA, Lyubimov SE, Kucherenko AS, Davankov VA. Russ. Chem. Bull. 2003; 52: 122
- 144i Wolfe JA, Hitchcock SR. Tetrahedron: Asymmetry 2010; 21: 2690
-
144j Gais H.-J, Eichelmann H, Spalthoff N, Gerhards F, Frank M, Raabe G. Tetrahedron: Asymmetry 1998; 9: 235
- 144k Tsarev VN, Konkin SI, Shyryaev AA, Davankov VA, Gavrilov KN. Tetrahedron: Asymmetry 2005; 16: 1737
-
145 Trost BM, Organ MG, O’Doherty GA. J. Am. Chem. Soc. 1995; 117: 9662
- 146 Ueda M, Hartwig JF. Org. Lett. 2010; 12: 92
- 147 Jegelka M, Plietker B. Org. Lett. 2009; 11: 3462
- 148 Jegelka M, Plietker B. Chem. Eur. J. 2011; 17: 10417
- 149a Dubbaka SR, Vogel P. Angew. Chem. Int. Ed. 2005; 44: 7674
- 149b Dubbaka SR, Vogel P. Tetrahedron Lett. 2006; 47: 3345
- 149c Dubbaka SR, Vogel P. Org. Lett. 2004; 6: 95
- 149d Dubbaka SR, Vogel P. J. Am. Chem. Soc. 2003; 125: 15292
- 149e Volla CM. R, Dubbaka SR, Vogel P. Tetrahedron 2009; 65: 504
- 150 Labadie SS. J. Org. Chem. 1989; 54: 2496
- 151 Bandgar BP, Bettigeri SV, Phopase J. Org. Lett. 2004; 6: 2105
- 152 Hu F, Lei X. ChemCatChem 2015; 7: 1539
- 153 Fu Y, Zhu W, Zhao X, Hügel H, Wu Z, Su Y, Du Z, Huang D, Hu Y. Org. Biomol. Chem. 2014; 12: 4295
- 154 Liu X, Chen X, Mohr JT. Org. Lett. 2015; 17: 3572
- 155a Yamaguchi J, Itami K, Yamaguchi AD. Angew. Chem. Int. Ed. 2012; 51: 8960
- 155b Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
- 155c Ackermann L. Chem. Rev. 2011; 111: 1315
- 155d Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
-
155e Jazzar R, Hitce J, Renaudat A, Sofack-Kreutzer J, Baudoin O. Chem. Eur. J. 2010; 16: 2654
- 155f Crabtree RH. Chem. Rev. 2010; 110: 575
- 155g Bergman RG. Nature 2007; 446: 391
- 155h Godula K, Sames D. Science 2006; 312: 67
- 156 Zhao X, Dimitrijevic E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466
- 157 Zhao X, Dong VM. Angew. Chem. Int. Ed. 2011; 50: 932
- 158 Xu Y, Liu P, Li SL, Sun P. J. Org. Chem. 2015; 80: 1269
- 159a Zhang D, Cui X, Zhang Q, Wu Y. J. Org. Chem. 2015; 80: 1517
- 159b Xia C, Wei Z, Shen C, Xu J, Yang Y, Su W, Zhang P. RSC Adv. 2015; 5: 52588
- 160 Xu YH, Wang M, Lu P, Loh TP. Tetrahedron 2013; 69: 4403
- 161 Ge B, Wang D, Dong W, Ma P, Li Y, Ding Y. Tetrahedron Lett. 2014; 55: 5443
- 162 Wu Z, Song H, Cui X, Pi C, Du W, Wu Y. Org. Lett. 2013; 15: 1270
- 163 Reddy VP, Qiu R, Iwasaki T, Kambe N. Org. Biomol. Chem. 2015; 13: 6803
- 164 Liang HW, Jiang K, Ding W, Yuan Y, Shuai L, Chen YC, Wei Y. Chem. Commun. 2015; 51: 16928
- 165 Saidi O, Marafie J, Ledger AE, Liu PM, Mahon MF, Kociok-Köhn G, Whittlesey MK, Frost CG. J. Am. Chem. Soc. 2011; 133: 19298
- 166 Liu J, Yu L, Zhuang S, Gui Q, Chen X, Wang W, Tan Z. Chem. Commun. 2015; 51: 6418
- 167 Rao WH, Shi BF. Org. Lett. 2015; 17: 2784
- 168 Liang S, Liu NW, Manolikakes G. Adv. Synth. Catal. 2016; 358: 159
- 169 Rao WH, Zhan BB, Chen K, Ling PX, Zhang ZZ, Shi BF. Org. Lett. 2015; 17: 3552
- 170 Tang X, Huang L, Xu Y, Yang J, Wu W, Jiang H. Angew. Chem. Int. Ed. 2014; 53: 4205
- 171 Kamijo S, Hirota M, Tao K, Watanabe M, Murafuji T. Tetrahedron Lett. 2014; 55: 5551
- 172 Sun K, Chen XL, Li X, Qu LB, Bi WZ, Chen X, Ma HL, Zhang ST, Han BW, Zhao YF, Li CJ. Chem. Commun. 2015; 51: 12111
- 173a Xiao F, Chen H, Xie H, Chen S, Yang L, Deng GJ. Org. Lett. 2014; 16: 50
- 173b Katrun P, Mueangkaew C, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. J. Org. Chem. 2014; 79: 1778
- 174 Nassoy AC. M, Raubo P, Harrity JP. Chem. Commun. 2015; 51: 5914
- 175 Qiu JK, Hao WJ, Wang DC, Wei P, Sun J, Jiang B, Tu SJ. Chem. Commun. 2014; 50: 14782
- 176 Xiao F, Chen S, Chen Y, Huang H, Deng GJ. Chem. Commun. 2015; 51: 652
- 177a Deeming AS, Emmett EJ, Richards-Taylor CS, Willis MC. Synthesis 2014; 46: 2701
- 177b Emmett EJ, Willis MC. Asian J. Org. Chem. 2015; 4: 602
- 177c Liu G, Fan C, Wu J. Org. Biomol. Chem. 2015; 13: 1592
- 177d Vogel P, Turks M, Bouchez L, Markovic D, Varela-Álvarez A, Sordo JÁ. Acc. Chem. Res. 2007; 40: 931
- 177e Floriańczyk Z, Raducha D. Pol. J. Chem. 1995; 69: 481
- 178a Burke SD In Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons; Chichester: 2001
- 178b Pelzer G, Herwig J, Keim W, Goddard R. Russ. Chem. Bull. 1998; 47: 904
- 178c Hoffman RV. Org. Synth. 1981; 60: 121
- 178d Malet-Sanz L, Madrzak J, Ley SV, Baxendale IR. Org. Biomol. Chem. 2010; 8: 5324
- 179a Hoffmann HM. R. Angew. Chem. Int. Ed. 1969; 8: 556
- 179b Rogic MM, Masilamani D. J. Am. Chem. Soc. 1977; 99: 5219
- 179c Markovic D, Varela-Alvarez A, Sordo JA, Vogel P. J. Am. Chem. Soc. 2006; 128: 7782
- 180 Wojcinski LM, Boyer MT, Sen A. Inorg. Chim. Acta 1998; 270: 8
- 181 Bouchez L, Vogel P. Synthesis 2002; 225
- 182 Marković D, Volla CM, Vogel P, Varela-Álvarez A, Sordo JA. Chem. Eur. J. 2010; 16: 5969
- 183a Deguin B, Roulet JM, Vogel P. Tetrahedron Lett. 1997; 38: 6197
- 183b Bouchez LC, Turks M, Dubbaka SR, Fonquerne F, Craita C, Laclef S, Vogel P. Tetrahedron 2005; 61: 11473
- 183c Bouchez LC, Dubbaka SR, Turks M, Vogel P. J. Org. Chem. 2004; 69: 6413
- 183d Exner CJ, Laclef S, Poli F, Turks M, Vogel P. J. Org. Chem. 2011; 76: 840
- 183e Huang XG, Vogel P. Synthesis 2002; 232
- 184a Bouchez LC, Vogel P. Chem. Eur. J. 2005; 11: 4609
- 184b Turks M, Huang X, Vogel P. Chem. Eur. J. 2005; 11: 465
- 184c Turks M, Fonquerne F, Vogel P. Org. Lett. 2004; 6: 1053
- 184d Narkevitch V, Vogel P, Schenk K. Helv. Chim. Acta 2002; 85: 1674
- 184e Huang XG, Craita C, Vogel P. J. Org. Chem. 2004; 69: 4272
- 184f Craita C, Didier C, Vogel P. Chem. Commun. 2007; 2411
- 185a Schlosser M. Organometallics in Synthesis. Third Manual . Wiley; Hoboken: 2013
- 185b Knochel P. Handbook of Functionalized Organometallics. Application and Synthesis. Wiley-VCH; Weinheim: 2005
- 186 Wu JP, Emeigh J, Su X.-P. Org. Lett. 2005; 7: 1223
- 187a Margraf N, Manolikakes G. J. Org. Chem. 2015; 80: 2582
- 187b Umierski N, Manolikakes G. Org. Lett. 2013; 15: 4972
- 188 Shavnya A, Coffey SB, Smith AC, Mascitti V. Org. Lett. 2013; 15: 6226
- 189 Shavnya A, Hesp KD, Mascitti V, Smith AC. Angew. Chem. Int. Ed. 2015; 54: 13571
- 190 Johnson MW, Bagley SW, Mankad NP, Bergman RG, Mascitti V, Toste FD. Angew. Chem. Int. Ed. 2014; 53: 4404
- 191 Woolven H, González-Rodríguez C, Marco I, Thompson AL, Willis MC. Org. Lett. 2011; 13: 4876
- 192 Deeming AS, Russell CJ, Hennessy AJ, Willis MC. Org. Lett. 2014; 16: 150
- 193 Rocke BN, Bahnck KB, Herr M, Lavergne S, Mascitti V, Perreault C, Polivkova J, Shavnya A. Org. Lett. 2014; 16: 154
- 194 Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2013; 52: 12679
- 195 Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2014; 53: 10204
- 196 Chen CC, Waser J. Org. Lett. 2015; 17: 736
- 197a Nguyen B, Emmett EJ, Willis MC. J. Am. Chem. Soc. 2010; 132: 16372
- 197b Emmett EJ, Richards-Taylor CS, Nguyen B, Garcia-Rubia A, Hayter BR, Willis MC. Org. Biomol. Chem. 2012; 10: 4007
- 198 Richards-Taylor CS, Blakemore DC, Willis MC. Chem. Sci. 2014; 5: 222
- 199 Liu X, Li W, Zheng D, Fan X, Wu J. Tetrahedron 2015; 71: 3359
- 200 Zheng D, An Y, Li Z, Wu J. Angew. Chem. Int. Ed. 2014; 53: 2451
- 201 Fan W, Su J, Shi D, Feng B. Tetrahedron 2015; 71: 6740
- 202 Ovenden SP. B, Capon RJ. J. Nat. Prod. 1999; 62: 1246
- 203 Baunach M, Ding L, Willing K, Hertweck C. Angew. Chem. Int. Ed. 2015; 54: 13279
- 204 Wendt EC In The Medical Record . Vol. 33. Shrady GF, Stedman TL. W. Wood; New York: 1888: 597