Ni-Catalyzed Decarboxylative Silylation of Alkynyl Carbonates: Access to Chiral Allenes via Enantiospecific Conversions
Kun Guo, Qian Zeng, Alba Villar‐Yanez, Carles Bó, Arjan W. Kleij
Abstract
A Ni-mediated decarboxylative silylation of alkynyl cyclic carbonates used as versatile propargylic surrogates is reported affording a wide range of highly substituted 2,3- and 3,4-allenol products in good yields. The formal cross-coupling between a tentative intermediate Ni(allenyl) and the silyl reagent was further extended to enantiospecific conversions providing access to chiral allene synthons. This protocol marks the first Ni-catalyzed propargylic silylation proceeding through an SN2′ manifold.
Topics & Concepts
SilylationChemistrySynthonAlleneCatalysisReagentSN2 reactionOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCatalytic Cross-Coupling Reactions