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

Angewandte Chemie
Guolin ChengJin-Quan Yu

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.

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Citations

Jul 12, 2018·Organic & Biomolecular Chemistry·Marcus WegmannThorsten Bach
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Jul 18, 2018·Chemistry : a European Journal·Ze-Shui LiuQianghui Zhou
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Sep 22, 2018·The Journal of Organic Chemistry·Weiwei LvGuolin Cheng

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