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Catalyst-Controlled 1,2- and 1,1-Arylboration of ?-Alkyl Alkenyl Arenes.

ABSTRACT: Two methods are reported for the 1,2- and 1,1-arylboration of ?-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 ?-hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.

SUBMITTER: Bergmann AM

PROVIDER: S-EPMC6823597 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Bergmann Allison M AM Dorn Stanna K SK Smith Kevin B KB Logan Kaitlyn M KM Brown M Kevin MK

Angewandte Chemie (International ed. in English) 20190109 6

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. ...[more]

PMID: 30521697

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