Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

Abstract

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

Key words

stereoselective synthesis - vinyl iodides - vinyl bromides - copper catalyst - halide-exchange reaction

• References


For a book, see:
• 1a Metal-Catalyzed Cross-Coupling Reactions . Diederich F. Stang PJ. Eds. Wiley-VCH; New York: 1998

For the use of vinyl iodides in various coupling reactions, see:
• 1b Kang S.-K. Kim J.-S. Choi S.-C. J. Org. Chem. 1997; 62: 4208
• 1c Kabir MS. Engelbrecht K. Polanowski R. Krueger SM. Ignasiak R. Rott M. Schwan WR. Stemper ME. Reed KD. Sherman D. Cook JM. Monte A. Bioorg. Med. Chem. Lett. 2008; 18: 5745
• 1d Tietze LF. Nobel T. Spescha M. J. Am. Chem. Soc. 1998; 120: 8971
• 1e Das B. Reddy GC. Balasubramanyam P. Salvanna N. Tetrahedron 2012; 68: 300
• 1f Shen R. Porco JA. Org. Lett. 2000; 2: 1333
• 1g Zhong P. Xiong ZX. Huang X. Synth. Commun. 2000; 30: 273
• 1h Reddy VP. Swapna K. Kumar AV. Rao KR. Synlett 2009; 2783
• 1i Reddy VP. Swapna K. Kumar AV. Rao KR. Tetrahedron Lett. 2010; 51: 293

For selected references, see:
• 2a Goodman MM. Chen P. Plisson C. Martarello L. Galt J. Votaw JR. Kilts CD. Malveaux G. Camp VM. Shi B. Ely TD. Howell L. McConathy J. Nemeroff CB. J. Med. Chem. 2003; 46: 925
• 2b Plisson C. McConathy J. Martarello L. Malveaux EJ. Camp VM. Williams L. Votaw JR. Goodman MM. J. Med. Chem. 2004; 47: 1122
• 2c Plisson C. Jarkas N. McConathy J. Voll RJ. Votaw J. Williams L. Howell LL. Kilts CD. Goodman MM. J. Med. Chem. 2006; 49: 942
• 2d Plisson C. Stehouwer JS. Voll RJ. Howell L. Votaw JR. Owens MJ. Goodman MM. J. Med. Chem. 2007; 50: 4553
• 3a Maryanoff BE. Reitz AB. Chem. Rev. 1989; 89: 863
• 3b Stork G. Zhao KA. Tetrahedron Lett. 1989; 30: 2173
• 3c Bestmann HJ. Rippel HC. Dostalek R. Tetrahedron Lett. 1989; 30: 5261
• 4a Augé J. Boucard V. Gil R. Lubin-Germain N. Picard J. Uziel J. Synth. Commun. 2003; 33: 3733
• 4b Takai K. Nitta K. Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
• 5a Cossy J. Bauer D. Bellosta V. Tetrahedron 2002; 58: 5909
• 5b Gonzalez IC. Forsyth CJ. J. Am. Chem. Soc. 2000; 122: 9099
• 6a Zhao Y. Snieckus V. Org. Lett. 2014; 16: 390
• 6b Huang Z. Negishi E.-I. Org. Lett. 2006; 8: 3675
• 7a Kadota I. Ueno H. Ohno A. Yamamoto Y. Tetrahedron Lett. 2003; 44: 8645
• 7b Uenishi J.-I. Kawahama R. Yonemitsu O. J. Org. Chem. 1998; 63: 8965
• 8 Gaviña F. Luis SV. Ferrer P. Costero AM. Marco JA. J. Chem. Res. 1986; 330

For selected reviews, see:
• 9a Sheppard TD. Org. Biomol. Chem. 2009; 7: 1043
• 9b Vigalok A. Chem. Eur. J. 2008; 14: 5102

For copper-mediated bromide–iodide exchange reactions, see:
• 9c Yamashita K.-I. Tsuboi M. Asano MS. Sugiura K.-I. Synth. Commun. 2012; 42: 170
• 9d Suzuki H. Aihara M. Yamamoto H. Takamoto Y. Ogawa T. Synthesis 1988; 236
• 9e Clark JH. Jones CW. J. Chem. Soc., Chem. Commun. 1987; 1409
• 9f Suzuki H. Kondo A. Inouye M. Ogawa T. Synthesis 1986; 121
• 9g Suzuki H. Kondo A. Ogawa T. Chem. Lett. 1985; 411
• 9h Lindley J. Tetrahedron 1984; 40: 1433
• 9i Bacon RG. R. Hill HA. O. J. Chem. Soc. 1964; 1097

For nickel-mediated bromide–iodide exchange reactions, see:
• 9j Yang SH. Li CS. Cheng CH. J. Org. Chem. 1987; 52: 691

For copper-catalyzed bromide–iodide exchange reactions, see:
• 9k Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002; 124: 14844
• 9l Meyer-Eppler G. Küchler L. Tenten C. Benkhäuser C. Brück S. Lützen A. Synthesis 2014; 46: 1085
• 9m Cannon KA. Geuther ME. Kelly CK. Lin S. MacArthur AH. R. Organometallics 2011; 30: 4067
• 9n Cristau H.-J. Ouali A. Spindler J.-F. Taillefer M. Chem. Eur. J. 2005; 11: 2483

For nickel-catalyzed bromide–iodide exchange reactions, see:
• 9o Takagi K. Hayama N. Okamoto T. Chem. Lett. 1978; 191
• 9p Takagi K. Hayama N. Inokawa S. Bull. Chem. Soc. Jpn. 1980; 53: 3691
• 9q Cant AA. Bhalla R. Pimlott SL. Sutherland A. Chem. Commun. 2012; 48: 3993
• 9r Wang JP. Pomerantz M. Tetrahedron Lett. 1995; 36: 2571
• 10 Li L. Liu W. Zeng H. Mu X. Cosa G. Mi Z. Li C.-J. J. Am. Chem. Soc. 2015; 137: 8328
• 11a Feng X. Qu Y. Han Y. Yu X. Bao M. Yamamoto Y. Chem. Commun. 2012; 48: 9468
• 11b Feng X. Li L. Yu X. Yamamoto Y. Bao M. Catal. Today 2016; 274: 129

Cu(I) salts and nitrogen-containing ligands were frequently utilized in C–C, C–N, and C–O coupling reactions. For books, see:
• 12a Catalyzed Carbon–Heteroatom Bond Formation . Yudin AK. Ed. Wiley-VCH; Weinheim: 2011
• 12b Catalysis Without Precious Metals . Bullock RM. Ed. Wiley-VCH; Weinheim: 2010
• 13a Sinha J. Layek S. Mandal CG. Bhattacharjee M. Chem. Commun. 2001; 1916
• 13b Murahashi S-I. Naota T. Tanigawa Y. Org. Synth. 1984; 62: 39
• 14 Pawluc P. Hreczycho G. Marciniec B. Org. Lett. 2009; 11: 3390
• 15 Lee GC. M. Tobias B. Holmes JM. Harcourt DA. Garst ME. J. Am. Chem. Soc. 1990; 112: 9330
• 16 Lorentzen M. Bayer A. Sydnes MO. Jørgensen KB. Tetrahedron 2015; 71: 8278
• 17 Mousseau JJ. Bull JA. Charette AB. Angew. Chem. Int. Ed. 2010; 49: 1115
• 18a Liu Y.-J. Zhang Z.-Z. Yan S.-Y. Liu Y.-H. Shi B.-F. Chem. Commun. 2015; 51: 7899
• 18b Xu R.-S. Yue L. Pan Y.-J. Tetrahedron 2012; 68: 5046
• 19 Carpita A. Ribecai A. Rossi R. Stabile P. Tetrahedron 2002; 58: 3673
• 20 Concellon JM. Rodriguez-Solla H. Huerta M. Eur. J. Org. Chem. 2002; 1839
• 21 Cheung LL. W. Yudin AK. Org. Lett. 2009; 11: 1281