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Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

ABSTRACT: Copper-catalyzed functionalization of terminal or 1,1-disubstituted alkenes with bis(pinacolato)diboron and methanol provides formal hydroboration products with exceptional regiocontrol favoring the branched isomer. Pairing this procedure with photocatalytic cross-couplings using iridium and nickel cocatalysis provides an effective, highly regioselective procedure for the hydroarylation of terminal alkenes.

SUBMITTER: Kerchner HA

PROVIDER: S-EPMC5189986 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Kerchner Hilary A HA Montgomery John J

Organic letters 20161027 21

Copper-catalyzed functionalization of terminal or 1,1-disubstituted alkenes with bis(pinacolato)diboron and methanol provides formal hydroboration products with exceptional regiocontrol favoring the branched isomer. Pairing this procedure with photocatalytic cross-couplings using iridium and nickel cocatalysis provides an effective, highly regioselective procedure for the hydroarylation of terminal alkenes. ...[more]

PMID: 27786484

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