Tebbe’s Reagent

Introduction

Tebbe’s reagent (1) is an organometallic compound and has found diverse applications in organic synthesis such as methylenation of carbonyl compounds, [1] synthesis of C-glycosides, [2] 1,6-disaccharides [3] and in the synthesis of intermediates, for example vinyl silanes [4] and allenyl­ketenes. [5] It is readily prepared by reacting titanocene dichloride and trimethylaluminum in toluene at r.t. (Scheme 1). [1] When Tebbe’s reagent is treated with a Lewis base, for example pyridine or THF, a highly reactive titanocene methylidene is generated. It methylenates a range of carboxylic and carbonic acid derivatives, presumably via oxatitanacyclobutane to furnish alkenes in a short period of time at room temperature and below. [6]

Scheme 1

References

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