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Synlett 2008(9): 1425-1426  
DOI: 10.1055/s-2008-1067022
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

(Trifluoromethyl)trimethylsilane (TMSCF3) - Ruppert’s Reagent: An Excellent Trifluoromethylation Agent

Renato Saldanha Bastos*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro (UFRJ), Avenida Athos da Silveira Ramos, Centro de Tecnologia, Bloco A, 6º andar. Ilha do Fundão, Cidade Universitária, Rio de Janeiro, CEP 21941-909, Brazil
e-Mail: bastosrs@ufrj.br;
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Publikationsdatum:
07. Mai 2008 (online)

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Introduction

The trifluoromethyl group (also known as a pseudohalide) in a molecule may bring about remarkable differences to its physical, chemical and biological properties. Applications in medicinal, agrochemical and materials sciences have been developed. [1,2,3]

(Trifluoromethyl)trimethylsilane (TMSCF3 or Me3SiCF3) was first synthesized by Ingo Ruppert in 1984. [4,5] The reaction involves the treatment of CF3Br and Me3SiCl in the presence of (Et2N)3P (Scheme [1] ).

Scheme 1

TMSCF3 can be used as an efficient nucleophilic trifluoromethylating agent. Many electrophiles can accept the CF3 group. It is generally necessary to use a fluoride source for reaction initiation. The fluoride ion acts as a nucleophile that attacks the trimethylsilane and facilitates the nucleophilic attack of the trifluoromethyl group on the eletrophilic center. Ruppert’s reagent trifluoromethylation can also be initiated by different Lewis bases or carbenes.

Another important function of TMSCF3 is the production of chiral trifluoromethylated alcohols when associated with chiral catalysts.

The reagent is a colorless liquid (bp 54-55 °C), commercially available as 0.5 M solution in THF, which can be handled at room temperature and in common laboratory glassware.