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Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

ABSTRACT: Organoboron "ate" complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.

SUBMITTER: Aparece MD

PROVIDER: S-EPMC6414219 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Aparece Mark D MD Gao Chenpeng C Lovinger Gabriel J GJ Morken James P JP

Angewandte Chemie (International ed. in English) 20181212 2

Organoboron "ate" complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours. ...[more]

PMID: 30444946

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