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Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift
Mark D Aparece1, Chenpeng Gao1, Gabriel J Lovinger1
1Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA, 02467, USA.
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.
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