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Vinylidenation of Organoboronic Esters Enabled by a Pd‐Catalyzed Metallate Shift
Author(s) -
Aparece Mark D.,
Gao Chenpeng,
Lovinger Gabriel J.,
Morken James P.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811782
Subject(s) - catalysis , stoichiometry , chemistry , palladium , chloride , organic chemistry , medicinal chemistry , polymer chemistry
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.