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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
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.