Synthesis 2012; 44(17): 2754-2762
DOI: 10.1055/s-0032-1316613
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Intermolecular Domino Reaction of gem-Dibromo­enynes with Anilines; A One-Pot Synthesis of Quinolines and Quinolinones

Tianhao Meng
a   Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, P. R. of China
,
Wen-Xiong Zhang
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728   Email: zfxi@pku.edu.cn
,
Hui-Jun Zhang
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728   Email: zfxi@pku.edu.cn
,
Yun Liang
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728   Email: zfxi@pku.edu.cn
,
Zhenfeng Xi*
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728   Email: zfxi@pku.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 14 May 2012

Accepted after revision: 11 June 2012

Publication Date:
23 July 2012 (online)


Abstract

An efficient domino process involving palladium-catalyzed amination of an alkenyl bromide, 1,5-H transfer, annulation via 6-exo-dig electrophilic cyclization, and palladium-catalyzed etherification, is described. This reaction provides an efficient one-pot synthesis of multi-substituted quinolines and quinolinones from gem-dibromoenynes and anilines.

Supporting Information