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Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C–H Alkenylation/Directing Group Migration

Mao, Hui; Chen, Jing; Zhang, Xiaoning; Yu, Na; Lu, Yangbin; Zhao, Fei; (2022) Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C–H Alkenylation/Directing Group Migration. ChemistrySelect , 7 (18) , Article e20220029. 10.1002/slct.202200292. Green open access

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Abstract

Herein we report the regio- and stereoselective synthesis of tetrasubstituted alkenes from N-carbamoyl indoles and alkynes via ruthenium(II)-catalyzed C−H alkenylation/directing group migration, in which the carbamoyl directing group is endowed with a dual role of auxiliary group and migrating acylation reagent via C−N bond cleavage. This method features broad substrate scope, high atom- and step-economy, good functional group tolerance and mild redox-neutral conditions at room temperature. A series of structurally diverse tetrasubstituted alkenes were synthesized in good to excellent yields, highlighting the efficiency of this method.

Type: Article
Title: Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C–H Alkenylation/Directing Group Migration
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/slct.202200292
Publisher version: https://doi.org/10.1002/slct.202200292
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.
Keywords: C−H activation, cascade reaction, directing group migration, ruthenium, tetrasubstituted alkene
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.ucl.ac.uk/id/eprint/10167674
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