Issue 1, 2021

Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones

Abstract

A rhodium-catalyzed tandem intermolecular hydroacylation of terminal alkyne-substituted secondary alcohols with chelating aldehydes and deconjugative isomerization of the resulting α,β-unsaturated ketones for the preparation of synthetically valuable 1,4-diketones is developed. Of note, the completely atom-economical protocol can be extended to the alkynyl alcohols with appropriate carbon chain length, from which 1,5-diketone and 1,6-diketone were obtained involving the short-range deconjugative isomerization. Given its robustness, broad substrate scope, and excellent regioselectivity, this approach provides a promising platform for the synthesis of diverse diketones.

Graphical abstract: Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones

Supplementary files

Article information

Article type
Research Article
Submitted
24 Sep 2020
Accepted
31 Oct 2020
First published
03 Nov 2020

Org. Chem. Front., 2021,8, 39-45

Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones

G. You, Z. Chang, J. Yan, C. Xia, F. Li and H. Li, Org. Chem. Front., 2021, 8, 39 DOI: 10.1039/D0QO01174F

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