Rhodium(III)-Catalyzed Oxidative Allylic C-H Indolylation via Nucleophilic Cyclization

Jiaqiong Sun; Kuan Wang; Peiyuan Wang; Guangfan Zheng; Xingwei Li

doi:10.1021/acs.orglett.9b01553

Rhodium(III)-Catalyzed Oxidative Allylic C-H Indolylation via Nucleophilic Cyclization

Org Lett. 2019 Jun 21;21(12):4662-4666. doi: 10.1021/acs.orglett.9b01553. Epub 2019 Jun 3.

Authors

Jiaqiong Sun¹, Kuan Wang¹, Peiyuan Wang¹, Guangfan Zheng¹, Xingwei Li^{1

2}

Affiliations

¹ Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering , Shaanxi Normal University (SNNU) , Xi'an 710062 , China.
² School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang 453007 , China.

PMID: 31184193
DOI: 10.1021/acs.orglett.9b01553

Abstract

Reported herein is a mild synthesis of 3-allylindoles via Rh(III)-catalyzed allylic C-H activation of olefins and coupling with o-alkynylanilines. The reaction proceeded via initial nucleophilic cyclization of o-alkynylanilines followed by oxidative coupling with allylic C-H bonds via an η³-allyl intermediate.