Issue 21, 2018

Regioselective indole C2-alkylation using β-CF3-substituted enones under redox neutral Rh(iii) catalysis

Abstract

Rhodium(III) catalyzed C–H alkylation at the C2-position of indole with β-trifluoromethyl-α,β-unsaturated ketones is described. The reactions proceed efficiently with low catalyst loading and a broad range of substrates with excellent functional group compatibility. The scale-up reaction was successfully achieved with 0.5 mol% of the Rh catalyst without significant decrease in the yield. This protocol provides direct access to pharmaceutically important indole derivatives containing a stereogenic carbon center bearing a CF3 functionality at the C2-position.

Graphical abstract: Regioselective indole C2-alkylation using β-CF3-substituted enones under redox neutral Rh(iii) catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
28 Aug 2018
Accepted
27 Sep 2018
First published
27 Sep 2018

Org. Chem. Front., 2018,5, 3133-3137

Regioselective indole C2-alkylation using β-CF3-substituted enones under redox neutral Rh(III) catalysis

B. Chaudhary, M. Diwaker and S. Sharma, Org. Chem. Front., 2018, 5, 3133 DOI: 10.1039/C8QO00932E

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