Issue 45, 2019

Catalytic enantioselective cross dehydrogenative coupling of sp3 C–H of heterocycles

Abstract

C–C bond formation in heterocycles via the direct coupling of C–H bonds, under oxidative conditions, classified as cross dehydrogenative coupling (CDC), is without doubt one of the most atom efficient methods for the functionalization of these molecules. The most common is the coupling at the position alpha to the heteroatom, owing to the stabilization of forming carbocation by the heteroatom. The corresponding asymmetric versions, except for a few isolated reports, have been rather evasive for several years. Optically active heterocycles with the chiral center alpha to the heteroatom are widely present in natural products and pharmaceuticals, thus making them an attractive synthetic target. Persistent efforts towards the asymmetric CDC of heterocycles since the beginning of this decade have led to several developments in this challenging area. Particularly, in the last few years, considerable progress has been witnessed in this field. This review summarizes the progress made in the area of asymmetric cross dehydrogenative coupling of heterocycles in recent years. The review covers the catalytic asymmetric CDC of sp3 C–H bonds of the heterocycles with various coupling partners and illustrates the different catalytic systems employed.

Graphical abstract: Catalytic enantioselective cross dehydrogenative coupling of sp3 C–H of heterocycles

Article information

Article type
Review Article
Submitted
30 Қыр. 2019
Accepted
04 Қар. 2019
First published
05 Қар. 2019

Org. Biomol. Chem., 2019,17, 9683-9692

Catalytic enantioselective cross dehydrogenative coupling of sp3 C–H of heterocycles

S. Gandhi, Org. Biomol. Chem., 2019, 17, 9683 DOI: 10.1039/C9OB02113B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements