title: Decarboxylative benzylations of alkynes and ketones.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
authors.forename: Robert R P
authors.initials: RR
authors.lastname: Torregrosa
authors.forename: Yamuna
authors.initials: Y
authors.lastname: Ariyarathna
authors.forename: Kalicharan
authors.initials: K
authors.lastname: Chattopadhyay
authors.forename: Jon A
authors.initials: JA
authors.lastname: Tunge
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D003432:Cross-Linking Reagents; D003653:Decarboxylation; D006571:Heterocyclic Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*
chemical_list: D000480:Alkynes; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D007659:Ketones; D001554:Benzene