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Issue 45, 2019
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Catalytic enantioselective cross dehydrogenative coupling of sp3 C–H of heterocycles

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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

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Publication details

The article was received on 30 Sep 2019, accepted on 04 Nov 2019 and first published on 05 Nov 2019


Article type: Review Article
DOI: 10.1039/C9OB02113B
Org. Biomol. Chem., 2019,17, 9683-9692

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

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

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