C−Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3‐Enynes | Zendy

Wang Ziyong | Zendy; Wu Jason | Zendy; Lamine Walid | Zendy; Li Bo | Zendy; Sotiropoulos JeanMarc | Zendy; Chrostowska Anna | Zendy; Miqueu Karinne | Zendy; Liu ShihYuan | Zendy

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C−Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3‐Enynes

Author(s) -

Wang Ziyong,

Wu Jason,

Lamine Walid,

Li Bo,

Sotiropoulos JeanMarc,

Chrostowska Anna,

Miqueu Karinne,

Liu ShihYuan

Publication year - 2021

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.202108534

Subject(s) - alkyne , nucleophile , boron , chemistry , catalysis , enyne , ligand (biochemistry) , electrophile , halogen , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , alkyl , receptor

Abstract A new family of carbon‐bound boron enolates, generated by a kinetically controlled halogen exchange between chlorocatecholborane and silylketene acetals, is described. These C−boron enolates are demonstrated to activate 1,3‐enyne substrates in the presence of a Pd 0 /Senphos ligand complex, resulting in the first examples of a carboboration reaction of an alkyne with enolate‐equivalent nucleophiles. Highly substituted dienyl boron building blocks are produced in excellent site‐, regio‐, and diastereoselectivity by the described catalytic cis ‐carboboration reaction.

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