Selective O-Cyclization of N-Methoxy Aryl Amides with CH2Br2 or 1,2-DCE via Palladium-Catalyzed C-H Activation

Wei-Hao Rao; Li-Li Jiang; Jin-Xiao Zhao; Xin Jiang; Guo-Dong Zou; Yu-Qiang Zhou; Lin Tang

doi:10.1021/acs.orglett.8b02678

Selective O-Cyclization of N-Methoxy Aryl Amides with CH₂Br₂ or 1,2-DCE via Palladium-Catalyzed C-H Activation

Org Lett. 2018 Oct 5;20(19):6198-6201. doi: 10.1021/acs.orglett.8b02678. Epub 2018 Sep 18.

Authors

Wei-Hao Rao^{1

2}, Li-Li Jiang¹, Jin-Xiao Zhao¹, Xin Jiang¹, Guo-Dong Zou¹, Yu-Qiang Zhou¹, Lin Tang¹

Affiliations

¹ College of Chemistry and Chemical Engineering , Xinyang Normal University , Xinyang 464000 , China.
² Henan Province Key Laboratory of Utilization of Non-Metallic Mineral in the South of Henan , Xinyang Normal University , Xinyang 464000 , China.

PMID: 30226060
DOI: 10.1021/acs.orglett.8b02678

Abstract

A selective O-cyclization of N-methoxy aryl amides with CH₂Br₂ or 1,2-DCE (1,2-dichloroethane) via palladium-catalyzed C-H activation has been described. New C(sp³)-O and C(sp²)-C(sp³) bonds are forged simultaneously with the assistance of an N-methoxy amide group, and good functional group tolerance in substrates is observed. Preliminary mechanistic investigations show that the process may involve a five-membered palladacycle intermediate.

Publication types

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