Synlett 2019; 30(11): 1329-1333
DOI: 10.1055/s-0037-1611825
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,3-Dihydrotryptamines from Amide Solvents and Acyclic Materials through Metal-Free Amidoalkylarylation of Unactivated Alkenes

Yubin Ji
a   Research Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China   Email: liuyj691@nenu.edu.cn
,
Siping Yang
b   Yunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China   Email: liangdq695@nenu.edu.cn
,
Shiyi Lin
b   Yunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China   Email: liangdq695@nenu.edu.cn
,
Yan Wang
b   Yunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China   Email: liangdq695@nenu.edu.cn
,
Chenfeng Ji
a   Research Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China   Email: liuyj691@nenu.edu.cn
,
Yingjie Liu*
a   Research Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China   Email: liuyj691@nenu.edu.cn
,
b   Yunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China   Email: liangdq695@nenu.edu.cn
› Author Affiliations
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (21702083), the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province, the Yunnan Ten Thousand Talent Program for Young Top-Notch Talents, and the Science Foundation Project of Harbin University of Commerce (18XN067).
Further Information

Publication History

Received: 12 March 2019

Accepted after revision: 24 April 2019

Publication Date:
03 May 2019 (online)


Abstract

The first synthesis of 2,3-dihydrotryptamines from acyclic materials and an exo-selective amidoalkylation/cyclization cascade of N-allyl anilines through α-C(sp3)–H functionalization of simple amides across unactivated alkenes are presented. This reaction proceeds in mixed aqueous media and under metal-free conditions and features a broad substrate scope and a simple operation.

Supporting Information

 
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