Tetrahedron letters

On the paradox of TiCl 4 reducing power: pinacol coupling and two-carbon homologation of carbonyl compounds

A Clerici, N Pastori, O Porta

Index: Clerici, Angelo; Pastori, Nadia; Porta, Ombretta Tetrahedron Letters, 2004 , vol. 45, # 9 p. 1825 - 1827

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Citation Number: 16

Abstract

TiCl4/DIPEA/CH2Cl2 reducing system promotes pinacol coupling and/or reduction to alcohol of aromatic aldehydes and carbonyl compounds activated towards reduction by an electron withdrawing group. In addition, bis homologation of these substrates is observed. An inner-sphere electron transfer from TiCl4 to DIPEA accounts for the products distribution.

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