Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis | Zendy

Renhe Li | Zendy; Yun Zhou | Zendy; Xiaolong Xu | Zendy; Guangbin Dong | Zendy

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Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis

Author(s) -

Renhe Li,

Yun Zhou,

Xiaolong Xu,

Guangbin Dong

Publication year - 2019

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b10857

Subject(s) - chemistry , norbornene , palladium , vicinal , catalysis , combinatorial chemistry , amide , thiophene , arsine , ligand (biochemistry) , organic chemistry , polymerization , phosphine , biochemistry , polymer , receptor

Herein we report a direct vicinal difunctionalization of thiophenes via the palladium/norbornene (Pd/NBE) cooperative catalysis. A series of mono- and disubstituted thiophenes can be difunctionalized site-selectively and regioselectively at the C4 and C5 positions in good yields, enabled by an arsine ligand and a unique amide-based NBE. The synthetic utility has been shown in derivatizations of complex bioactive compounds and an open-flask gram-scale preparation. Preliminary results have been obtained in the difunctionalization of furans and a direct C4-selective arylation of 2-substituted thiophenes.

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