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Palladium‐Catalyzed Direct α‐Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates
Author(s) -
Yuen On Ying,
Chen Xiangmeng,
Wu Junyu,
So Chau Ming
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000176
Subject(s) - chemistry , aryl , catalysis , palladium , steric effects , alkylation , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
The first general palladium‐catalyzed α‐arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. Pd(OAc) 2 associated with XPhos serves as the effective catalyst to facilitate this reaction. A broad range of electron‐rich, ‐neutral, ‐deficient, and sterically hindered aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles bearing different substituents to give the corresponding products in good to excellent yields. Catalyst loading down to 0.1 mol‐% Pd was achieved, and 22 unprecedented compounds were synthesized from 43 demonstrated examples using this method. Its applicability with the modification of biological phenolic compounds was successfully demonstrated. The Pd/XPhos system catalyzed the α‐arylation and followed by alkylation in one‐pot sequential conditions, resulting in the direct synthesis of compounds containing quaternary center‐ and deuterium‐containing compounds in good to excellent yields.