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A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones

Carmelo E. Iacono, Thomas C. Stephens, Teena S. Rajan and Graham Pattison*

*Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, U.K., Email: g.pattisonbrighton.ac.uk

C. E. Iacono, T. C. Stephens, T. S. Rajan, G. Pattison, J. Am. Chem. Soc., 2018, 140, 2036-2040.

DOI: 10.1021/jacs.7b12941 (free Supporting Information)


Abstract

A transition-metal-free coupling of esters with geminal bis(boron) compounds provides an α,α-bis(enolate) equivalent which can be trapped with electrophiles including alkyl halides and fluorinating agents. This presents an efficient, convergent synthetic strategy for the synthesis of α,α-difunctionalized ketones.

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Key Words

acylation, fluorination, NFSI, alkylation


ID: J48-Y2018