An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction

作者:Geoghegan Kimberly; Kelleher Susan; Evans Paul*
来源:Journal of Organic Chemistry, 2011, 76(7): 2187-2194.
DOI:10.1021/jo200023r

摘要

Herein is described an operationally simple process concerning the observation that, following either inter-, or intramolecular Heck olefination, stirring of the so formed substituted alkenyl product under an atmosphere of hydrogen efficiently effects alkene hydrogenation. Overall this two-operation, one-pot "reductive Heck" sequence is notable since direct reductive Heck processes, using additives such as formate salts, are restricted to a limited range of substrates. In total 25 examples are reported (yields ranging from 0 to 95%), which were selected in order to probe the scope and limitations of this method. Finally, the utility of this sequence was demonstrated in a short synthesis of the calcimimetic agent, cinacalcet.

  • 出版日期2011-4-1