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meta ‐C−H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst
Author(s) -
Cheng Guolin,
Wang Peng,
Yu JinQuan
Publication year - 2017
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.201704411
Subject(s) - isoquinoline , chemistry , palladium , alkylation , ligand (biochemistry) , catalysis , substrate (aquarium) , sulfonate , homogeneous catalysis , functional group , combinatorial chemistry , medicinal chemistry , organic chemistry , sodium , receptor , polymer , biochemistry , oceanography , geology
Palladium(II)‐catalyzed meta ‐C−H arylation and alkylation of benzylsulfonamide using 2‐carbomethoxynorbornene (NBE‐CO 2 Me) as a transient mediator are realized by using a newly developed electron‐deficient directing group and isoquinoline as a ligand. This protocol features broad substrate scope and excellent functional‐group tolerance. The meta ‐substituted benyzlsulfonamides can be readily transformed into sodium sulfonates, sulfonate esters, and sulfonamides, as well as styrenes by Julia‐type olefination. The unique impact of the isoquinoline ligand underscores the importance of subtle matching between ligands and the directing groups.