Vinylidenation of Organoboronic Esters Enabled by a Pd‐Catalyzed Metallate Shift. Issue 2 (12th December 2018)

• Record Type: Journal Article
• Authors: Aparece, Mark D.; Gao, Chenpeng; Lovinger, Gabriel J.; Morken, James P.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 2(2019)
• Page Start: 592
• Page End: 595
• Publication Date: 2018-12-12
• Subjects: allyl complexes -- boron -- homogeneous catalysis -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201811782
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : α‐Methylene organoboronic esters : These compounds are prepared in a catalytic fashion for precursor boronic esters by a Pd‐catalyzed rearrangement of the derived "ate" complexes.