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. (Request a copy)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) |
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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) |