Palladium-catalyzed direct C-H arylation of 3-aryl-2H-benzo[1,2,4]thiadiazine 1,1-dioxides: an efficient strategy to the synthesis of benzothiadiazine-1,1-dioxide derivatives

Dongyin Wang; Wei Liu; Fei Yi; Yongli Zhao; Junmin Chen

doi:10.1039/c5ob02196k

Palladium-catalyzed direct C-H arylation of 3-aryl-2H-benzo[1,2,4]thiadiazine 1,1-dioxides: an efficient strategy to the synthesis of benzothiadiazine-1,1-dioxide derivatives

Org Biomol Chem. 2016 Feb 14;14(6):1921-4. doi: 10.1039/c5ob02196k.

Authors

Dongyin Wang¹, Wei Liu¹, Fei Yi², Yongli Zhao², Junmin Chen¹

Affiliations

¹ Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, PR China and Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Nanchang, 330022, PR China.
² Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, PR China.

PMID: 26751270
DOI: 10.1039/c5ob02196k

Abstract

A new palladium-catalyzed benzothiadiazine-1,1-dioxide direct arylation of C(sp(2))-H bonds is described. 3-Aryl-2H-benzo[1,2,4]thiadiazine 1,1-dioxides react with various aryl iodides to give the corresponding mono-arylation products 3-(biphenyl-2-yl)-2H-benzo[1,2,4]thiadiazine 1,1-dioxides with high reactivity and regioselectivity in the presence of AgOAc. Remarkedly, the addition of TFA is crucial to improve the arylation yield.

Publication types

Research Support, Non-U.S. Gov't