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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811782
Subject(s) - catalysis , chemistry , stoichiometry , palladium , chloride , medicinal chemistry , organic 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.