Issue 7, 2023

Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols

Abstract

The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp3)–C(sp2) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.

Graphical abstract: Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
12 Jan 2023
Accepted
20 Feb 2023
First published
21 Feb 2023

Org. Chem. Front., 2023,10, 1705-1709

Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols

X. Zhang, Z. Luo, T. Liu and Q. Li, Org. Chem. Front., 2023, 10, 1705 DOI: 10.1039/D3QO00049D

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