Production of silated haloarenes by selective silylation of poly

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

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C07F 708

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060841176

ABSTRACT:
Lithiated haloarenes, although useful as intermediates in the synthesis of various end products, can be hazardous to prepare since unstable, shock sensitive compounds can be formed during lithiation of haloarenes. To avoid this problem, a reaction of a polyhaloarene with a hydrocarbyl lithium compound is conducted in the presence of another reactant so that the lithiated haloarene, if formed at all, exists as a transitory intermediate in low concentration. In this way, transitory lithiated haloarene which may be, and presumably is, formed in the reaction is converted into a non-hazardous functionally-substituted haloarene essentially as soon as such lithiated haloarene is formed. Thus, an arene having a halogen atom of atomic number greater than 9 substituted on at least two non-adjacent carbon atoms is concurrently reacted with a non-fluoro halotrihydrocarbylsilane and a hydrocarbyl lithium compound, in proportions such that a haloarene having at least one trihydrocarbylsilyl ring substituent is formed.

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Kurata et al., "Tandem Reactions of N,N-Dialkylamides With Organolithium Compounds and Cyclopentadiene. A New Efficient Synthesis of Pentafulvenes", Tetrahedron Letters, Jun. 1993, vol. 34, No. 21, pp. 3445-3448.

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