Radical Chain Reduction of Alkylboron Compounds with Catechols

Villa, Giorgio; Povie, Guillaume; Renaud, Philippe (2011). Radical Chain Reduction of Alkylboron Compounds with Catechols. Journal of the American Chemical Society, 133(15), pp. 5913-5920. Washington, D.C.: American Chemical Society 10.1021/ja110224d

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The conversion of alkylboranes to the corresponding alkanes is classically performed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 degrees C). We report here a mild radical procedure for the transformation of organoboranes to alkalies. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B-alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 degrees C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Renaud, Philippe

ISSN:

0002-7863

Publisher:

American Chemical Society

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 14:26

Last Modified:

06 Dec 2013 13:31

Publisher DOI:

10.1021/ja110224d

Web of Science ID:

000290358200063

URI:

https://boris.unibe.ch/id/eprint/9394 (FactScience: 215125)

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