Atroposelective Synthesis of C−N Vinylindole Atropisomers by Palladium‐Catalyzed Asymmetric Hydroarylation of 1‐Alkynylindoles

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 repor...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-11, Vol.62 (45), p.e202312930-e202312930
Main Authors: Zhan, Li‐Wen, Lu, Chuan‐Jun, Feng, Jia, Liu, Ren‐Rong
Format: Article
Language:English
Subjects:
Alkynes
Enantiomers
Functional groups
Palladium
Palladium compounds
Reagents
Regioselectivity
Stereoselectivity
Synthesis
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202312930