Open AccessAlcohols and Water as Reducing Agents in Radical Reactions
Author(s) -
Davide Pozzi,
Philippe Renaud
Publication year - 2007
Publication title -
chimia
Language(s) - English
Resource type - Journals
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2007.151
Subject(s) - reducing agent , boron , alcohol , chemistry , dissociation (chemistry) , tin , hydrogen bond , combinatorial chemistry , derivative (finance) , photochemistry , bond dissociation energy , organic chemistry , molecule , business , finance
The radical reduction of B-alkylcatecholboranes into alkanes using alcohols and water as hydrogen atom source is described. This process involves a completely unexpected mechanism: the alcohol (or water) complexed to a borate derivative acts as a reducing agent. The complexation activates the alcohol resulting in a decrease of the O–H bond dissociation energy. This approach offers promising opportunities for the development of tin-free radical reducing agent. Closely related reports from the recent literature involving boron and titanium derivatives are also presented.