Synthesis 2018; 50(15): 2981-2989
DOI: 10.1055/s-0037-1609444
special topic
© Georg Thieme Verlag Stuttgart · New York

Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles

Xinxin Zhao
a  State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen 518005, P. R. of China   Email: xiawj@hit.edu.cn
,
Ming Chen
a  State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen 518005, P. R. of China   Email: xiawj@hit.edu.cn
,
Binbin Huang
a  State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen 518005, P. R. of China   Email: xiawj@hit.edu.cn
,
Chao Yang
a  State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen 518005, P. R. of China   Email: xiawj@hit.edu.cn
,
Yuan Gao
b  School of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai 264005, P. R. of China
,
a  State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen 518005, P. R. of China   Email: xiawj@hit.edu.cn
› Author Affiliations
We are grateful for the financial support from China NSFC (Nos. 21372055, 21472030 and 21672047) and SKLUWRE (No. 2018DX02).
Further Information

Publication History

Received: 09 February 2018

Accepted after revision: 13 March 2018

Publication Date:
08 May 2018 (eFirst)

Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleo­philic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.

Supporting Information

 
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