Synthesis 2019; 51(07): 1655-1661
DOI: 10.1055/s-0037-1611355
paper
© Georg Thieme Verlag Stuttgart · New York

C3-Allylation of Indoles via an Iridium-Catalyzed Branch-Selective Ring-Opening Reaction of Vinylcyclopropanes

Lei Yu
,
Zi-Qi Zhu
,
Meng Sun
,
Guang-Jian Mei*
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: guangjianM@jsnu.edu.cn
,
Feng Shi  *
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: guangjianM@jsnu.edu.cn
› Institutsangaben
We much appreciate the financial support from NSFC (21772069 and 21702077), the Natural Science Foundation of Jiangsu Province (BK20160003 and BK20170227), Six Kinds of Talents Project of Jiangsu Province (SWYY-025), and Natural Science Foundation of Xuzhou City (KH17021).
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Publikationsverlauf

Received: 25. August 2018

Accepted after revision: 24. Oktober 2018

Publikationsdatum:
03. Dezember 2018 (online)


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Abstract

An iridium-catalyzed branch-selective ring-opening reaction of vinylcyclopropanes with indoles has been established, which afforded C3-allylindoles in generally good to excellent yields (up to 95%). Considering that no wastes were generated in the whole process and branch-selective ring-opening reaction of vinylcyclopropanes was rarely reported, this strategy not only can be regarded as a highly atom-economic approach for C3-allylindoles, but also will greatly enrich the chemistry of vinylcyclopropanes.

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