Decarboxylative Benzylations of Alkynes and Ketones

作者:Torregrosa Robert R P; Ariyarathna Yamuna; Chattopadhyay Kalicharan; Tunge Jon A*
来源:Journal of the American Chemical Society, 2010, 132(27): 9280-9282.
DOI:10.1021/ja1035557

摘要

Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

  • 出版日期2010-7-14