Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation
Top Cited Papers
- 6 June 2011
- journal article
- review article
- Published by Wiley in Angewandte Chemie
- Vol. 50 (27), 6004-6011
- https://doi.org/10.1002/anie.201100145
Abstract
In the last decade, an increasing number of useful catalytic reductions of carboxylic acid derivatives with hydrosilanes have been developed. Notably, the combination of an appropriate silane and catalyst enables unprecedented chemoselectivity that is not possible with traditional organometallic hydrides or hydrogenation catalysts. For example, amides and esters can be reduced preferentially in the presence of ketones or even aldehydes. We believe that catalytic hydrosilylations will be used more often in the future in challenging organic syntheses, as the reaction procedures are straightforward, and the reactivity of the silane can be fine‐tuned. So far, the synthetic potential of these processes has clearly been underestimated. They even hold promise for industrial applications, as inexpensive and readily available silanes, such as polymethylhydrosiloxane, offer useful possibilities on a larger scale.This publication has 70 references indexed in Scilit:
- Catalytic hydrogenation of polar organic functionalities based on Ru-mediated heterolytic dihydrogen cleavageChemical Communications, 2007
- Reduction of amides with silanes catalyzed by MoO2Cl2Journal of Molecular Catalysis A: Chemical, 2007
- Silane/MoO2Cl2 as an efficient system for the reduction of estersJournal of Molecular Catalysis A: Chemical, 2006
- Preparation and Molecular and Electronic Structures of Iron(0) Dinitrogen and Silane Complexes and Their Application to Catalytic Hydrogenation and HydrosilationJournal of the American Chemical Society, 2004
- Hydrosilylation of aromatic nitriles promoted by solvated rhodium atom-derived catalystsJournal of Molecular Catalysis A: Chemical, 1999
- An Inexpensive Air-Stable Titanium-Based System for the Conversion of Esters to Primary AlcoholsThe Journal of Organic Chemistry, 1995
- Titanocene-Catalyzed Reduction of Esters Using Polymethylhydrosiloxane as the Stoichiometric ReductantThe Journal of Organic Chemistry, 1994
- An air-stable catalyst system for the conversion of esters to alcoholsThe Journal of Organic Chemistry, 1992
- A catalytic method for the reduction of esters to alcoholsJournal of the American Chemical Society, 1991
- Sur Quelques aspects de la reactivite des hydrogenosilanes en chimie organiquePure and Applied Chemistry, 1966