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

Full text not available from this repository.

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:

05 Dec 2022 14:07

Publisher DOI:

10.1021/ja110224d

Web of Science ID:

000290358200063

URI:

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

Actions (login required)

Edit item Edit item
Provide Feedback