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Arylboron Compounds as Acid Catalysts in Organic Synthetic Transformations
Author(s) -
Ishihara Kazuaki,
Yamamoto Hisashi
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199903)1999:3<527::aid-ejoc527>3.0.co;2-r
Subject(s) - chemistry , catalysis , lewis acids and bases , borane , organic chemistry , organic synthesis , boron , olefin fiber , organic base , metallocene , lewis acid catalysis , brønsted–lowry acid–base theory , polymerization , polymer
Arylboron compounds, Ar n B(OH) 3– n ( n = 1–3), bearing electron‐withdrawing aromatic groups such as triarylboranes, diarylborinic acids, and arylboronic acids represent a new class of air‐stable and water‐tolerant Lewis acid or Brønsted acid catalysts in organic synthesis. In particular, while tris(pentafluorophenyl)borane has primarily been used as a co‐catalyst in metallocene‐mediated olefin polymerization, its potential as a Lewis acid catalyst for organic transformation is now much more extensive. Diarylborinic acids and arylboronic acids have shown themselves to be powerful tools in the design of chiral boron catalysts. This article provides a comprehensive summary of the organic transformations catalyzed by arylboron compounds as acids.