Issue 12, 2021

Access to the C2 C–H olefination, alkylation and deuteration of indoles by rhodium(iii) catalysis: an opportunity for diverse syntheses

Abstract

A concise approach for the synthesis of structurally diverse indoles enabled by RhIII-catalyzed switchable C2 C–H olefination and alkylation of N-quinolinyl indoles with alkenes as well as highly efficient C–H deuteration is described. The reaction can be conducted under practical reaction conditions, with a broad substrate scope and good tolerance of various functional groups. The potential value of this synthetic methodology is shown by the diverse late-stage modification of the products, thereby providing a straightforward route to access functionalized indoles, especially indole-based P,N ligands.

Graphical abstract: Access to the C2 C–H olefination, alkylation and deuteration of indoles by rhodium(iii) catalysis: an opportunity for diverse syntheses

Supplementary files

Article information

Article type
Research Article
Submitted
25 Jan 2021
Accepted
23 Mar 2021
First published
25 Mar 2021

Org. Chem. Front., 2021,8, 3032-3040

Access to the C2 C–H olefination, alkylation and deuteration of indoles by rhodium(III) catalysis: an opportunity for diverse syntheses

J. Wu, B. Qian, L. Lu, H. Yang, Y. Shang and J. Zhang, Org. Chem. Front., 2021, 8, 3032 DOI: 10.1039/D1QO00133G

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