Cs₂CO₃-Mediated Regio- and Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates

This paper is dedicated to Professor Majid M. Heravi on the occasion of his 68^th birthday.

Abstract

A highly selective synthesis of (Z)-1-bromo-1-sulfonyl alkenes via Cs₂CO₃-promoted sulfonylation of 1,1-dibromo-1-alkenes with sodium sulfinates is described. Notably, using excess amounts of Cs₂CO₃ and sodium sulfinate in such a reaction regenerated the parent aldehyde. Interestingly, the reaction of 1-(2,2-dibromovinyl)-2-nitrobenzene in the presence of sulfinates and Cs₂CO₃ produced isatin. The Sonogashira cross coupling of synthesized (Z)-1-bromo-1-sulfonyl alkenes with phenylacetylene gave selectively the corresponding sulfonylalkynyl alkenes.

Key words

1,1-dibromo-1-alkenes - sodium sulfonates - regioselective - vinyl sulfone - cesium carbonate - isatin

Publication History

Received: 10 July 2020

Accepted after revision: 22 August 2020

Article published online:
06 October 2020

• References

• 1a Dunny E, Doherty W, Evans P, Malthouse JP. G, Nolan D, Knox AJ. J. Med. Chem. 2013; 56: 6638
• 1b Rueeger H, Lueoend R, Rogel O, Rondeau J.-M, Möbitz H, Machauer R, Jacobson L, Staufenbiel M, Desrayaud S, Neumann U. J. Med. Chem. 2012; 55: 3364
• 1c Xu Y, Tang X, Hu W, Wu W, Jiang H. Green Chem. 2014; 16: 3720
• 1d Shen Y, Zificsak CA, Shea JE, Lao X, Bollt O, Li X, Lisko JG, Theroff JP, Scaife CL, Ator MA. J. Med. Chem. 2015; 58: 1140
• 1e Woo SY, Kim JH, Moon MK, Han S.-H, Yeon SK, Choi JW, Jang BK, Song HJ, Kang YG, Kim JW. J. Med. Chem. 2014; 57: 1473
• 1f Doherty W, James J, Evans P, Martin L, Adler N, Nolan D, Knox A. Org. Biomol. Chem. 2014; 12: 7561
• 1g Turnbull AP, Ioannidis S, Krajewski WW, Pinto-Fernandez A, Heride C, Martin AC, Tonkin LM, Townsend EC, Buker SM, Lancia DR. Nature 2017; 550: 481
• 1h Aziz J, Messaoudi S, Alami M, Hamze A. Org. Biomol. Chem. 2014; 12: 9743
• 2a Kumamoto H, Deguchi K, Wagata T, Furuya Y, Odanaka Y, Kitade Y, Tanaka H. Tetrahedron 2009; 65: 8007
• 2b Zhu Q, Lu Y. Org. Lett. 2009; 11: 1721
• 2c Arjona O, Menchaca R, Plumet J. Org. Lett. 2001; 3: 107
• 2d Noshi MN, El-Awa A, Torres E, Fuchs PL. C. J. Am. Chem. Soc. 2007; 129: 11242
• 2e Wardrop DJ, Fritz J. Org. Lett. 2006; 8: 3659
• 2f Sulzer-Mossé S, Alexakis A, Mareda J, Bollot G, Bernardinelli G, Filinchuk Y. Chem. Eur. J. 2009; 15: 3204
• 2g López-Pérez A, Robles-Machín R, Adrio J, Carretero JC. Angew. Chem. Int. Ed. 2007; 46: 9261
• 2h Chang M.-Y, Cheng Y.-C. Org. Lett. 2016; 18: 1682
• 2i Chang M.-Y, Cheng Y.-C, Lu Y.-J. Org. Lett. 2014; 16: 6252
• 2j Wu JC, Gong LB, Xia Y, Song RJ, Xie YX, Li JH. Angew. Chem. Int. Ed. 2012; 51: 9909
• 2k Fuchs P, Braish T. Chem. Rev. 1986; 86: 903
• 2l Simpkins NS. Tetrahedron 1990; 46: 6951
• 2m Nájera C, Yus M. Tetrahedron 1999; 55: 10547
• 2n Enders D, Müller SF, Raabe G, Runsink J. Eur. J. Org. Chem. 2000; 879
• 2o Alba A.-NR, Companyó X, Rios R. Chem. Soc. Rev. 2010; 39: 2018
• 2p De Lucchi O, Pasquato L. Tetrahedron 1988; 44: 6755
• 2q Chinkov N, Majumdar S, Marek I. J. Am. Chem. Soc. 2003; 125: 13258
• 3a Fang Y, Luo Z, Xu X. RSC Adv. 2016; 6: 59661
• 3b Shen Z.-J, Wu Y.-N, He C.-L, He L, Hao W.-J, Wang A.-F, Tu S.-J, Jiang B. Chem. Commun. 2018; 54: 445
• 3c Zheng D, Yu J, Wu J. Angew. Chem. Int. Ed. 2016; 55: 11925
• 3d García-Domínguez A, Müller S, Nevado C. Angew. Chem. Int. Ed. 2017; 56: 9949
• 3e Li X, Xu Y, Wu W, Jiang C, Qi C, Jiang H. Chem. Eur. J. 2014; 20: 7911
• 3f Liang S, Zhang RY, Wang G, Chen SY, Yu XQ. Eur. J. Org. Chem. 2013; 7050
• 3g Xi Y, Dong B, McClain EJ, Wang Q, Gregg TL, Akhmedov NG, Petersen JL, Shi X. Angew. Chem. Int. Ed. 2014; 53: 4657
• 3h Wu C, Yang P, Fu Z, Peng Y, Wang X, Zhang Z, Liu F, Li W, Li Z, He W. J. Org. Chem. 2016; 81: 10664
• 3i Luo Z, Fang Y, Zhao Y, Xu X, Feng C, Li Z, Zhang X, He J. Tetrahedron Lett. 2016; 57: 4105
• 4a Skillinghaug B, Rydfjord J, Odell LR. Tetrahedron Lett. 2016; 57: 533
• 4b Nair V, Augustine A, Suja T. Synthesis 2002; 2259
• 4c Xie L.-Y, Peng S, Liu F, Chen G.-R, Xia W, Yu X, Li W.-F, Cao Z, He W.-M. Org. Chem. Front. 2018; 5: 2604
• 4d Peng S, Song Y.-X, He J.-Y, Tang S.-S, Tan J.-X, Cao Z, Lin Y.-W, He W.-M. Chin. Chem. Lett. 2019; 30: 2287
• 5a Chelucci G. Chem. Rev. 2011; 112: 1344
• 5b Heravi MM, Asadi S, Nazari N, Lashkariani BM. Curr. Org. Chem. 2015; 19: 2196
• 5c Ji Y, Zhong N, Kang Z, Yan G, Zhao M. Synlett 2018; 29: 209
• 5d Zhao M, Kuang C, Yang Q, Cheng X. Tetrahedron Lett. 2011; 52: 992
• 5e Soderquist JA, Leon G, Colbert JC, Martinez I. Tetrahedron Lett. 1995; 36: 3119
• 5f Fang Y.-Q, Lautens M. J. Org. Chem. 2008; 73: 538
• 5g Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
• 6a Corey E, Fuchs P. Tetrahedron Lett. 1972; 3769
• 6b Singh RM, Nandini D, Bharadwaj KC, Gupta T, Singh RP. Org. Biomol. Chem. 2017; 15: 9979
• 6c Ramirez F, Desai NB, McKelvie N. J. Am. Chem. Soc. 1962; 84: 1745
• 7a Liu J.-S, Zhu Y.-L, Yu C.-M, Zhou Y.-Z, Han Y.-Y, Wu F.-W, Qi B.-F. Can. J. Chem. 1986; 64: 837
• 7b Lin S.-T, Lee C.-C, Liang DW. Tetrahedron 2000; 56: 9619
• 8a Zeng X, Hu Q, Qian M, Negishi E.-i. J. Am. Chem. Soc. 2003; 125: 13636
• 8b Zeng X, Qian M, Hu Q, Negishi EI. Angew. Chem. Int. Ed. 2004; 43: 2259
• 9 Webber R, Peglow TJ, Nobre PC, Barcellos AM, Roehrs JA, Schumacher RF, Perin G. Tetrahedron Lett. 2016; 57: 4128
• 10 Shi J.-C, Zeng X, Negishi E.-I. Org. Lett. 2003; 5: 1825
• 11a Reed MA, Chang MT, Snieckus V. Org. Lett. 2004; 6: 2297
• 11b Paraja M, Barroso R, Cabal MP, Valdés C. Adv. Synth. Catal. 2017; 359: 1058
• 11c Chelucci G. Chem. Commun. 2014; 50: 4069
• 12 Jouvin K, Coste A, Bayle A, Legrand F, Karthikeyan G, Tadiparthi K, Evano G. Organometallics 2012; 31: 7933
• 13 Pang Y, Kojima R, Ito H. Org. Biomol. Chem. 2018; 16: 6187
• 14 Chen W, Li P, Miao T, Meng L.-G, Wang L. Org. Biomol. Chem. 2013; 11: 420
• 15 Xu XH, Taniguchi M, Wang X, Tokunaga E, Ozawa T, Masuda H, Shibata N. Angew. Chem. Int. Ed. 2013; 52: 12628
• 16 Li W, Yin G, Huang L, Xiao Y, Fu Z, Xin X, Liu F, Li Z, He W. Green Chem. 2016; 18: 4879
• 17 Wu C, Yang P, Fu Z, Peng Y, Wang X, Zhang Z, Liu F, Li W, Li Z, He W. J. Org. Chem. 2016; 81: 10664
• 18 Yoshimatsu M, Hasegawa J. J. Chem. Soc., Perkin Trans. 1 1997; 211
• 19 Fisher B, Lepage RJ, White JM, Ye Y, Krenske EH, Rizzacasa MA. Org. Biomol. Chem. 2017; 15: 5529
• 20 Schirmeister T, Kesselring J, Jung S, Schneider TH, Weickert A, Becker J, Lee W, Bamberger D, Wich PR, Distler U, Tenzer S, Johé P, Hellmich UA, Engels B. J. Am. Chem. Soc. 2016; 138: 8332
• 21 Salehi P, Shiri M. Adv. Synth. Catal. 2019; 361: 118
• 22 CCDC 1918812 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 23 Gotsko MD, Sobenina LN, Vashchenko AV, Trofimov BA. Tetrahedron Lett. 2018; 59: 4231
• 24 Marien N, Reddy BN, De Vleeschouwer F, Goderis S, Van Hecke K, Verniest G. Angew. Chem. Int. Ed. 2018; 57; 5660
• 25 Zhong G. Angew. Chem. Int. Ed. 2003; 42: 4247
• 26a Ramirez F, Desai NB, McKelvie N. J. Am. Chem. Soc. 1962; 84: 1745
• 26b Nandini D, Asthana M, Mishra K, Singh RP, Singh RM. Tetrahedron Lett. 2014; 55: 6257