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Rhodium(III)-Catalyzed C–H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes

Wu, Xiaowei; Lu, Yangbin; Qiao, Jin; Dai, Wenhao; Jia, Xiuwen; Ni, Hangcheng; Zhang, Xiaoning; ... Zhao, Fei; + view all (2020) Rhodium(III)-Catalyzed C–H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes. Organic Letters , 22 (23) pp. 9163-9168. 10.1021/acs.orglett.0c03077. Green open access

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Abstract

An efficient Rh(III)-catalyzed C-H alkenylation/directing group migration cascade between indoles and alkynes for the assembly of tetrasubstituted alkenes is reported. The carbamoyl directing group migrates to the carbon of the alkene moiety of the products through rare Rh-catalyzed C-N bond cleavage after the C-H alkenylation step and thus acts as an internal amidation reagent. This protocol shows broad substrate scope, excellent regio/stereoselectivity, and good to excellent yields.

Type: Article
Title: Rhodium(III)-Catalyzed C–H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.orglett.0c03077
Publisher version: https://doi.org/10.1021/acs.orglett.0c03077
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery-pp.ucl.ac.uk/id/eprint/10167630
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