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