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Meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

ABSTRACT: Palladium(II)-catalyzed meta-C-H arylation and alkylation of benzylsulfonamide using 2-carbomethoxynorbornene (NBE-CO2 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.

SUBMITTER: Cheng G

PROVIDER: S-EPMC5553125 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

Cheng Guolin G Wang Peng P Yu Jin-Quan JQ

Angewandte Chemie (International ed. in English) 20170609 28

Palladium(II)-catalyzed meta-C-H arylation and alkylation of benzylsulfonamide using 2-carbomethoxynorbornene (NBE-CO<sub>2</sub> 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 ...[more]

PMID: 28516518

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