Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions

Hong-Yu Zhang; Jianjun Chen; Cong-Cong Lu; Ya-Ping Han; Yuecheng Zhang; Jiquan Zhao

doi:10.1021/acs.joc.1c01207

Visible-Light-Induced C(sp²)-C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions

J Org Chem. 2021 Sep 3;86(17):11723-11735. doi: 10.1021/acs.joc.1c01207. Epub 2021 Aug 9.

Authors

Hong-Yu Zhang¹, Jianjun Chen¹, Cong-Cong Lu¹, Ya-Ping Han¹, Yuecheng Zhang¹, Jiquan Zhao¹

Affiliation

¹ School of Chemical Engineering and Technology, Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300130, P. R. China.

PMID: 34369160
DOI: 10.1021/acs.joc.1c01207

Abstract

Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp²)-C(sp³) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy)₃Cl₂·6H₂O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted N-heterocycles with extensive functional group compatibility in 40-86% yields.