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Synlett 2011(14): 2100-2101  
DOI: 10.1055/s-0030-1260963
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Phenylsilane

Yong-Xiao Li*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: yongxiao0325@sina.com;
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Publikationsdatum:
21. Juli 2011 (online)

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Introduction

Phenylsilane (PhSiH3) is an organosilane and has been extensively used in organic synthesis as a mild and environmentally benign reducing agent. It is a clear, colorless, volatile liquid which boils at 120 ˚C. [¹] When heated to decomposition it emits acrid smoke and irritating vapors. It reacts violently with water, so the preparation of phenylsilane must be performed in a reaction vessel connected with a vacuum system by a standard ground glass joint. It has been used for the hydrosilylation reduction of ketones and aldehydes to give the corresponding alcohols. [²] It was also found to be an efficient reagent for selective reduction of quinoline to dihydroquinoline, [³] reductive Michael cyclization, [4] and reductive aldol reaction. [5] The reductive coupling of aldimines has been achieved by the use of a combination of PhSiH3 and titanium isopropoxide [Ti(Oi-Pr)4]. [6] Reductions of organic halides to dehalogenated ­alkanes with the In(OAc)3-PhSiH3 system are readily accomplished. [7] It can also act as an in situ carboxylic acid activating agent to prepare carboxamides and peptides from carboxylic acids and amines. [8]

Phenylsilane is commercially available now. It can be readily prepared by reduction of phenyltrichlorosilane with lithium aluminum hydride in ether. [9]

Scheme 1