Atroposelective Synthesis of C−N Vinylindole Atropisomers by Palladium-Catalyzed Asymmetric Hydroarylation of 1-Alkynylindoles
Li-Wen Zhan
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chuan-Jun Lu
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Jia Feng
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ren-Rong Liu
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
Search for more papers by this authorLi-Wen Zhan
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chuan-Jun Lu
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Jia Feng
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ren-Rong Liu
College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071 China
Search for more papers by this authorGraphical Abstract
The enantioselective hydroarylation of 1-alkynylindoles with organoborons for the synthesis of chiral C−N atropisomers is presented. A wide variety of vinylindole atropisomers were synthesized in excellent regioselectivity, stereoselectivity (Z-selectivity), and enantioselectivity under mild reaction conditions.
Abstract
Transition-metal-catalyzed hydroarylation of unsymmetrical internal alkynes remains challenging because of the difficulty in controlling regioselectivity and stereoselectivity. Moreover, the enantioselective hydroarylation of alkynes using organoboron reagents has not been reported. Herein, we report for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons for the synthesis of chiral C−N atropisomers. A series of rarely reported vinylindole atropisomers was synthesized with excellent regio-, stereo- (Z-selectivity), and enantioselectivity under mild reaction conditions. The ready availability of organoborons and alkynes and the simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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