A Qualitative Analysis of a “Bora-Brook Rearrangement”: The Ambident Reactivity of Boryl-Substituted Alkoxide Including the Carbon-to-Oxygen Migration of a Boryl Group

A bora-Brook rearrangement, i.e., the migration of boryl group from a carbon to an oxygen atom in an isolated α-boryl-substituted alkoxide, was examined, and decisive factors for the acceleration of this reaction are disclosed. In this rearrangement, the boryl-substituted alkoxide exhibited ambiphil...

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Published inJournal of the American Chemical Society Vol. 138; no. 10; pp. 3548 - 3552
Main Authors Kisu, Haruki, Sakaino, Hirotoshi, Ito, Fumihiro, Yamashita, Makoto, Nozaki, Kyoko
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.03.2016
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Summary:A bora-Brook rearrangement, i.e., the migration of boryl group from a carbon to an oxygen atom in an isolated α-boryl-substituted alkoxide, was examined, and decisive factors for the acceleration of this reaction are disclosed. In this rearrangement, the boryl-substituted alkoxide exhibited ambiphilic reactivity toward electrophiles to afford two types of products, which are electrophiles bound either at the oxygen or at the carbon atom. Using polar solvents, a saturated backbone of the boron-containing heterocycle, or larger alkali metal cations resulted in a significantly increased reaction rate of base-catalyzed isomerization of α-borylbenzyl alcohol including the bora-Brook rearrangement.
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b00283