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Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates
Author(s) -
He Tao,
Li Bin,
Liu LiChuan,
Wang Jing,
Ma WenPeng,
Li GuangYu,
Zhang QingWei,
He Wei
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804480
Subject(s) - geminal , hydroboration , chemoselectivity , intramolecular force , borylation , chemistry , catalysis , ligand (biochemistry) , combinatorial chemistry , substrate (aquarium) , coupling reaction , stereochemistry , medicinal chemistry , organic chemistry , aryl , biochemistry , alkyl , receptor , oceanography , geology
A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross‐coupling, hydroboration, which has been rarely documented.