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Since the original report in 2004, phosphonium coupling has emerged as a new, mild, efficient, chemoselective and versatile methodology for the direct C–C, C–N, C–O, and C–S bond formations of unactivated and unprotected tautomerizable heterocycles. Phosphonium coupling proceeds via C–OH bond activation of a tautomerizable heterocycle with a phosphonium salt (PyBroP or BOP), and subsequent functionalization with either a nucleophile through SNAr displacement or an organometallic through transition-metal-catalyzed cross-coupling. As the first direct bond formation via C–OH bond activation, phosphonium coupling offers a powerful and practical methodology for chemical synthesis that features operational simplicity, functionality compatibility, and broad substrate scope. Its attractive protecting-group-free direct bond formation involving a domino multiple-step process in a single step provides unique and facile access to many biologically important heterocycles (1-5).

References:

1. Fu-An Kang, William V. Murray, Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA.; August, 2004; American Chemical Society, Washington, D.C., 2004; ORGN-702. 2. Fu-An Kang, Jason Kodah, Qunying Guan, Xiaobing Li, William V. Murray, J. Org. Chem. 2005, 70, 1957. 3. Fu-An Kang, Zhihua Sui, William V. Murray, J. Am. Chem. Soc. 2008, 130, 11300. 4. Fu-An Kang, Zhihua Sui, William V. Murray, Eur. J. Org. Chem. 2009, 461. 5. Fu-An Kang, James C. Lanter, Caozhong Cai, Zhihua Sui, William V. Murray, Chem. Comm. 2010, 46, 1347.