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Issue 35, 2020
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A direct route to six and seven membered lactones via γ-C(sp3)–H activation: a simple protocol to build molecular complexity

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Abstract

Lactones comprise a class of valuable compounds having biological as well as industrial importance. Development of a methodology to synthesize such molecules directly from readily available materials such as aliphatic carboxylic acid is highly desirable. Herein, we have reported synthesis of δ-lactones and ε-lactones via selective γ-C(sp3)–H activation. The γ-C–H bond containing aliphatic carboxylic acids provide six or seven membered lactones depending on the olefin partner in the presence of a palladium catalyst. A mechanistic investigation suggests that C–H activation is the rate-determining step. Further transformations of the lactones have been carried out to showcase the applicability of the present strategy.

Graphical abstract: A direct route to six and seven membered lactones via γ-C(sp3)–H activation: a simple protocol to build molecular complexity

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Supplementary files

Article information


Submitted
05 Jun 2020
Accepted
19 Aug 2020
First published
19 Aug 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 9697-9702
Article type
Edge Article

A direct route to six and seven membered lactones via γ-C(sp3)–H activation: a simple protocol to build molecular complexity

J. Das, P. Dolui, W. Ali, J. P. Biswas, H. B. Chandrashekar, G. Prakash and D. Maiti, Chem. Sci., 2020, 11, 9697
DOI: 10.1039/D0SC03144E

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