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Catalyst‐Controlled 1,2‐ and 1,1‐Arylboration of α‐Alkyl Alkenyl Arenes
Author(s) -
Bergmann Allison M.,
Dorn Stanna K.,
Smith Kevin B.,
Logan Kaitlyn M.,
Brown M. Kevin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812533
Subject(s) - enantioselective synthesis , chemistry , catalysis , alkyl , hydride , organometallic chemistry , cascade , medicinal chemistry , organic chemistry , migratory insertion , combinatorial chemistry , stereochemistry , metal , chromatography
Two methods are reported for the 1,2‐ and 1,1‐arylboration of α‐methyl vinyl arenes. In the case of 1,2‐arylboration, the formation of a quaternary center occurred through a rare cross‐coupling reaction of a tertiary organometallic complex. 1,1‐Arylboration was enabled by catalyst optimization and occurred through a β‐hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.