Aryltriolborates as Air- and Water-Stable Bases for Wittig Olefination

Wenhua Huang; Shuang-Hong Zhao; Ning Xu

doi:10.1055/s-0034-1378919

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(03): 359-366
DOI: 10.1055/s-0034-1378919

paper

Aryltriolborates as Air- and Water-Stable Bases for Wittig Olefination

Wenhua Huang*

Department of Chemistry, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27403475 eMail: huangwh@tju.edu.cn

,

Shuang-Hong Zhao

Department of Chemistry, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27403475 eMail: huangwh@tju.edu.cn

,

Ning Xu

Department of Chemistry, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27403475 eMail: huangwh@tju.edu.cn

› Institutsangaben

Abstract

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Abstract

Tetrabutylammonium aryltriolborates have been synthesized in 37–66% yield by a one-pot procedure from arylboronic acids, 1,1,1-tris(hydroxymethyl)ethane, and aqueous tetrabutylammonium hydroxide. The aryltriolborates can be used as bases in Wittig reactions of aromatic aldehydes with all three types of phosphorus ylides: stabilized and semistabilized ylides can be generated at room temperature, and nonstabilized ylides at 120 °C (bath temperature).

Key words

tetrabutylammonium aryltriolborates - Wittig olefination - phosphorus ylides - organic bases - organoboron compounds

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Referenzen

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