Synlett 2009(19): 3221-3223  
DOI: 10.1055/s-0029-1218382
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Petasis Reagent

Carine Vaxelaire
Faculté des Sciences Pharmaceutiques et Biologiques, Avenue de l′Observatoire 4, 75270 Paris, France
e-Mail: carine.vaxelaire@univ-paris5.fr;
Further Information

Publication History

Publication Date:
13 November 2009 (online)

Introduction

The Petasis reagent [¹] (dimethyl titanocene, Cp2TiMe2) is readily prepared by the reaction of methylmagnesium chloride [²] or methyllithium [³] with titanocene dichloride. It is used for transforming carbonyl groups to terminal al­kenes, [4] like the Tebbe reagent or Wittig reaction. Unlike the Wittig reaction, the Petasis reagent can react with a wide range of carbonyls, such as aldehydes, ketones, ­esters, and lactones including enolizable and acid-labile substrates. The Petasis reagent is also non-pyrophoric, relatively air- and water-stable, and can be used directly as a solution in toluene-THF.

The active olefinating reagent, Cp2TiCH2, can be prepared by heating the Petasis reagent in toluene or THF to 60-75 ˚C. The Petasis reaction can also be promoted by microwave irradiation.

Scheme 1

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