(NH₄)₂S₂O₈-Mediated Diiodination of Alkynes with Iodide in Water: Stereospecific Synthesis of (E)-Diiodoalkenes

Abstract

A new approach to the stereospecific diiodination of alkynes under mild conditions has been developed. This protocol employs ammonium persulfate as an oxidant and iodide as an iodine source, and provides a highly efficient and general method for the preparation of a broad range of (E)-diiodoalkenes in water.

Key words

persulfate salts - diiodination - alkenes - alkynes - water

• References


For selective application of vic-dihaloalkene, see:
• 1a Poulsen TB, Dickmeiss G, Overgaard J, Jorgensen KA. Angew. Chem. Int. Ed. 2008; 47: 4687
• 1b Jiang B, Tian H, Huang Z.-G, Xu M. Org. Lett. 2008; 10: 2737
• 1c Ranu BC, Adak L, Chattopadhyay K. J. Org. Chem. 2008; 73: 5609
• 1d Simard-Mercier J, Jiang JL, Ho ML, Flynn AB, Ogilvie WW. J. Org. Chem. 2008; 73: 5899
• 1e Ranu BC, Chattopadhyay K. Org. Lett. 2007; 9: 2409
• 1f Lemay AB, Vulic KS, Ogilvie WW. J. Org. Chem. 2006; 71: 3615
• 1g Sun C, Camp JE, Weinreb SM. Org. Lett. 2006; 8: 1779
• 1h Negishi E, Alimardanov A, Xu C. Org. Lett. 2000; 2: 65
• 1i Bellina F, Colzi F, Mannina L, Rossi R, Viel S. J. Org. Chem. 2003; 68: 10175
• 1j Ghosh AK, Bilcer G, Schiltz G. Synthesis 2001; 2203
• 1k List B, Castello C. Synlett 2001; 1687

For selective application of gem-dihaloalkene, see:
• 2a Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
• 2b Coste A, Couty F, Evano G. Org. Lett. 2009; 11: 4454
• 2c Okutani M, Mori Y. J. Org. Chem. 2009; 74: 442
• 2d Tan Z, Negishi E. Angew. Chem. Int. Ed. 2006; 45: 762
• 2e Zeng X, Qian M, Hu Q, Negishi E. Angew. Chem. Int. Ed. 2004; 43: 2259
• 2f Ogasawara M, Ikeda H, Hayashi T. Angew. Chem. Int. Ed. 2000; 39: 1042
• 2g Xu J, Burton DJ. J. Org. Chem. 2006; 71: 3743
• 2h Zeng X, Hu Q, Qian M, Negishi E. J. Am. Chem. Soc. 2003; 125: 13636
• 2i Hwang GT, Son HS, Ku JK, Kim BH. J. Am. Chem. Soc. 2003; 125: 11241
• 2j Shen W, Kunzer A. Org. Lett. 2002; 4: 1315
• 3a Barluenga J, Montserrat JM, Flórez J. J. Org. Chem. 1993; 58: 5976
• 3b Staab HA, Shin HJ. Chem. Ber. 1977; 110: 631
• 3c Huynh C, Linstrumelle G. Tetrahedron 1988; 44: 6337
• 3d Wright ME, Lowe-Ma CK. Organometallics 1990; 9: 347
• 3e Hénaff N, Whiting A. J. Chem. Soc., Perkin Trans. 1 2000; 395 ; and references therein
• 4a Hollins RA, Campos MP. A. J. Org. Chem. 1979; 44: 3931
• 4b Heasley VL. D, Shellhamer F, Heasley LE, Yaeger DB. J. Org. Chem. 1980; 45: 4649
• 4c Raffa G, Belot S, Balme G, Monteiro N. Org. Biomol. Chem. 2011; 9: 1474
• 5a Larson S, Luidhardt T, Kabalka GW, Pagni RM. Tetrahedron Lett. 1988; 29: 35
• 5b Hondrogiannis G, Lee LC, Kabalka GW, Pagni RM. Tetrahedron Lett. 1989; 30: 2069
• 5c Pagni RM, Kabalka GW, Boothe R, Gaetano K, Stewart LJ, Conaway R, Dial C, Gray D, Larson S, Luidhard T. J. Org. Chem. 1988; 53: 4477
• 5d Duan J, Dolbier WR. Jr, Chen Q.-Y. J. Org. Chem. 1998; 63: 9486

For some selected examples, see:
• 6a Jereb M, Zupan M, Stavber S. Chem. Commun. 2004; 2614
• 6b Li J.-H, Xie Y.-X, Yin D.-L. Green Chem. 2002; 4: 505
• 6c Pavlinac J, Zupan M, Stavber S. Org. Biomol. Chem. 2007; 5: 699
• 6d Hiegel GA, Bayne CD, Ridley B. Synth. Commun. 2003; 33: 1997
• 6e Li J.-H, Xie Y.-X, Yin D.-L, Jiang H.-F. Chin. J. Org. Chem. 2003; 21: 714
• 6f Terent’ev AO, Borisov DA, Krylov IB, Nikishin GI. Synth. Commun. 2007; 37: 3151
• 6g Stavber G, Iskra J, Zupan M, Stavber S. Adv. Synth. Catal. 2008; 350: 2921
• 6h Madabhushi S, Jillella R, Mallu KK. R, Godala KR, Vangipuram VS. Tetrahedron Lett. 2013; 54: 3993

For reviews, see:
• 7a Li C.-J. Chem. Rev. 1999; 93: 2023
• 7b Li C.-J. Chem. Rev. 2005; 105: 3095
• 7c Herrerías CI, Yao X, Li Z, Li C.-J. Chem. Rev. 2007; 107: 2546
• 7d Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
• 7e Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
• 7f Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
• 8a Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
• 8b Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
• 8c Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
• 8d Lindström UM. Organic Reactions in Water . Blackwell; Oxford: 2007
• 8e Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
• 8f Uozumi Y, Yamada YM. A. Chem. Rec. 2009; 9: 51
• 8g Raj M, Singh VK. Chem. Commun. 2009; 6687
• 8h Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
• 9 Jiang Q, Sheng W, Guo C. Green Chem. 2013; 15: 2175
• 10 Wang J.-Y, Jiang Q, Guo C.-C. Synth. Commun. 2014; 44: 3130
• 11a Negishi E In Handbook of Organopalladium Chemistry for Organic Synthesis . Vol. I. Negishi E. Wiley-Interscience; New York: 2002: 213-1119
• 11b Metal-Catalyzed Cross-Coupling Reactions . de Meijere A, Diederich F. Wiley-VCH; New York: 2004. ; and references therein
• 11c Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486
• 12 Schuh K, Glorius F. Synthesis 2007; 2297
• 13 Liang Y, Tao L.-M, Zhang Y.-H, Li J.-H. Synthesis 2008; 3988
• 14 Kimura T, Nishimura Y, Ishida N, Momochi H, Yamashita H, Satoh T. Tetrahedron Lett. 2013; 54: 1049
• 15 Li J.-H, Tang S. Synth. Commun. 2005; 35: 105
• 16a Jin Z. Nat. Prod. Rep. 2006; 23: 464
• 16b Yeh VS. C. Tetrahedron 2004; 60: 11995
• 16c Donelly DM. X, Meegan MJ In Comprehensive Heterocyclic Chemistry . Vol. 4. Katrikzky AR, Rees CW. Pergamon; Oxford: 1984: 657-712
• 16d Mahmoud MM, Ali HI, Ahn KH, Damaraju A, Samala S, Pulipati VK, Kolluru S, Kendall DA, Lu D. J. Med. Chem. 2013; 56: 7965
• 17a Nicolaou KC, Smith AL, Yue EW. Proc. Natl. Acad. Sci. U.S.A. 1993; 90: 5881
• 17b Kar M, Basak A. Chem. Rev. 2007; 107: 2861
• 17c Vanghn TH. Union Carbide Corp., Belg. 1963; 631: 355
• 18a Rudi A, Schleyer M, Kashman Y. J. Nat. Prod. 2000; 63: 1434
• 18b El-Jaber N, Estevez-Braun A, Ravelo AG, Munoz-Munoz O, Rodriguez-Afonso A, Murguia JR. J. Nat. Prod. 2003; 66: 722
• 18c Zein N, Sinha AM, McGahren WJ, Ellestad GA. Science 1988; 240: 1198
• 18d Iverson SL, Uetrecht JP. Chem. Res. Toxicol. 2001; 14: 175
• 19 Podgoršek A, Zupan M, Iskra J. Angew. Chem. Int. Ed. 2009; 48: 8424
• 20 Ide M, Yauchi Y, Shiogai R, Iwasawa T. Tetrahedron 2014; 70: 8532
• 21 Luo L, Resch D, Wilhelm C, Young CN, Halada GP, Gambino RJ, Grey CP, Goroff NS. J. Am. Chem. Soc. 2011; 133: 19274