Molecule of the Month
February 2011
4-tert-Butylcatechol

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, i.e. treatment with a carboxylic acid at high temperature (>150 C). We have recently developed a mild radical procedure for the transformation of organoboranes to alkanes where 4-tert-butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atom.

This work was carried out in the group of Prof. Philippe Renaud.

References:

  • G. Villa, G. Povie and P. Renaud;
    "Radical Chain Reduction of Alkylboron Compounds with Catechols"
    J. Am. Chem. Soc., 133, 59135920, (2011); doi:10.1021/ja110224d.