Synthesis 2014; 46(15): 2057-2064
DOI: 10.1055/s-0033-1338622
paper
© Georg Thieme Verlag Stuttgart · New York

Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions

Xixian Pan
a  Department of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134856   Email: yehao7171@shu.edu.cn
,
Xiaolong Wan
b  School of Materials Science and Engineering, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China
c  State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: xiewq@mail.sioc.ac.cn
,
Xin Yu
a  Department of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134856   Email: yehao7171@shu.edu.cn
,
Hui Zhang*
a  Department of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134856   Email: yehao7171@shu.edu.cn
,
Weiqing Xie*
c  State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: xiewq@mail.sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 28 February 2014

Accepted after revision: 25 March 2014

Publication Date:
23 April 2014 (eFirst)

Abstract

A decarboxylative hydroamination cascade reaction of 3-arylpropiolic acids with N-heterocycles under transition-metal-free conditions was developed. 3-Arylpropiolic acids were found to react smoothly with a range of N-heterocycles under the effect of t-BuOK to afford N-vinyl heterocycles in moderate to excellent yields. This reaction represents the first decarboxylative hydroamination of 3-arylpropiolic acids without the aid of a transition-metal catalyst.

Supporting Information

 
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