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Asymmetric Dearomatization of Indole by Palladium/PC‐Phos‐Catalyzed Dynamic Kinetic Transformation
Author(s) -
Chu Haoke,
Cheng Jie,
Yang Junfeng,
Guo YinLong,
Zhang Junliang
Publication year - 2020
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.202010164
Subject(s) - xantphos , palladium , indole test , chemistry , kinetic resolution , catalysis , phosphine , yield (engineering) , combinatorial chemistry , ligand (biochemistry) , organic chemistry , enantioselective synthesis , materials science , receptor , biochemistry , metallurgy
A palladium‐catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3‐arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand ( PC‐Phos ) as the co‐ligands. This method could deliver various spiro[indene‐1,3′‐indole] compounds in good yields (up to 95 % yield) with up to 98 % ee . The salient features of the transformation include the use of readily available substrates, ease of scale‐up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.