Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart ˙ New York Desulfurizing Difluorination Reaction of Benzyl Sulfides Using IF5 Tadahito Fukuhara, Shoji Hara*Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, JapanFax: +81(11)7066556; e-Mail: shara@eng.hokudai.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract A desulfurizing difluorination reaction of benzyl sulfides having a functional group such as an ester, a ketone, a nitrile, or an amide was performed by a reaction with IF5. Consequently, gem-difluoro compounds could be obtained selectively. Key words fluorination - desulfurization - hypervalent iodine - oxidation - sulfide Full Text References References 1a Welch JT. Tetrahedron 1987, 43: 3123 1b Welch JT. Eswarakrishnan S. Fluorine in Bioorganic Chemistry Wiley; New York: 1991. 1c Resnati G. Tetrahedron 1993, 49: 9385 1d Hiyama T. In Organofluorine Compounds Springer; Berlin: 2000. Chap. 5. 2a Tozer MJ. Herpin TF. Tetrahedron 1996, 52: 8619 2b Konas DW. Coward JK. Org. Lett. 1999, 1: 2105 2c Dubowchik GM. Vrudhula VM. Dasgupta B. Ditta J. Chen T. Sheriff S. Sipman K. Witmer M. Tredup J. Vyas DM. Verdoorn TA. Bollini S. Vinitsky A. Org. Lett. 2001, 3: 3987 3a Greaney MF. Motherwell WB. Tetrahedron Lett. 2000, 41: 4463 3b Motherwell WB. Greaney MF. Edmunds JJ. Steed JW. J. Chem. Soc., Perkin Trans. 1 2002, 2816 3c Ayuba S. Yoneda N. Fukuhara T. Hara S. Bull. Chem. Soc. Jpn. 2002, 75: 1597 As for the review, see: 3d Dawood KM. Tetrahedron 2004, 60: 1435 3e Fuchigami T. Tajima T. J. Fluorine Chem. 2005, 126: 181 4a Differding E. Rüegg GM. Lang RW. Tetrahedron Lett. 1991, 32: 1779 4b Kotoris CC. Chen M.-J. Taylor SD. J. Org. Chem. 1998, 63: 8052 4c Pravst I. Zupan M. Stavber S. Synthesis 2005, 3140 5a Middleton WJ. Bingham EM. J. Org. Chem. 1980, 45: 2883 5b Hägele G. Haas A. J. Fluorine Chem. 1996, 76: 15 5c Lai GS. Pez GP. Pesaresi RJ. Prozonic FM. Cheng H. J. Org. Chem. 1999, 64: 7048 5d Singh RP. Shreeve JM. Org. Lett. 2001, 3: 2713 5e Singh RP. Shreeve JM. J. Org. Chem. 2001, 66: 6263 5f Singh RP. Shreeve JM. J. Org. Chem. 2003, 68: 6063 6a Murakami S. Kim S. Ishii H. Fuchigami T. Synlett 2004, 815 6b Murakami S. Ishii H. Tajima T. Fuchigami T. Tetrahedron 2006, 62: 3761 6c Guo Y. Shreeve JM. Chem. Commun. 2007, 3583 6d Nicolaou KC. Estrada AA. Freestone GC. Lee SH. Alvarez-Mico X. Tetrahedron 2007, 63: 6088 6e Boyer N. Gloznec P. Nanteuil GD. Jubault P. Quirion J.-C. Tetrahedron 2007, 63: 12532 As for the review, see: 6f Amii H. Uneyama K. In Fluorine-Containing Synthons Soloshonok VA. American Chemical Society; Washington DC: 2005. p.455 6g Sato K. Omote M. Ando A. Kumadaki I. In Fluorine-Containing Synthons Soloshonok VA. American Chemical Society; Washington DC: 2005. p.476 6h Uneyama K. Organofluorine Chemistry Blackwell; Oxford: 2006. p.223 6i Wang X.-J. Zhang F. Liu J.-T. Tetrahedron 2008, 64: 1731 7a Ayuba S. Fukuhara T. Hara S. Org. Lett. 2003, 5: 2873 7b Ayuba S. Hiramatsu C. Fukuhara T. Hara S. Tetrahedron 2004, 60: 11445 8 Hiyama T. In Organofluorine Compounds Springer; Berlin: 2000. Chap. 2. ; and references cited therein 9a Kanie K. Tanaka Y. Suzuki K. Kuroboshi M. Hiyama T. Bull. Chem. Soc. Jpn. 2000, 73: 471 9b Reddy VP. Alleti R. Perambuduru MK. Welz-Biermann U. Buchholz H. Prakash GKS. Chem. Commun. 2005, 654 9c Cohen O. Rozen S. Tetrahedron 2008, 64: 5362 10a Brigaud T. Laurent E. Tetrahedron Lett. 1990, 31: 2287 10b Furuta S. Kuroboshi M. Hiyama T. Tetrahedron Lett. 1995, 36: 8243 11 Rozen S. Brand M. J. Org. Chem. 1986, 51: 222