Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions

(Chemical Equation Presented) Herein we report a study involving the homogeneous catalytic reduction of unsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of N...

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Autores principales:	Gaviglio, Carina Del Valle, Doctorovich, Fabio Ariel
Publicado:	2008
Materias:	Chemical reactions Hydrogen Iron Nonmetals Olefins Organic compounds Organic solvents Aqueous solutions Catalytic amounts Catalytic reductions Chemical equations Water-organic solvent mixtures Solutions alkene derivative carbon hydrogen isotope organic solvent water aqueous solution article catalysis chemical reaction cost kinetics pressure reduction kinetics stereospecificity
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v73_n14_p5379_Gaviglio http://hdl.handle.net/20.500.12110/paper_00223263_v73_n14_p5379_Gaviglio
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00223263_v73_n14_p5379_Gaviglio
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spelling	paper:paper_00223263_v73_n14_p5379_Gaviglio2023-06-08T14:49:35Z Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions Gaviglio, Carina Del Valle Doctorovich, Fabio Ariel Chemical reactions Hydrogen Iron Nonmetals Olefins Organic compounds Organic solvents Aqueous solutions Catalytic amounts Catalytic reductions Chemical equations Water-organic solvent mixtures Solutions alkene derivative carbon hydrogen isotope organic solvent water aqueous solution article catalysis chemical reaction cost kinetics pressure reduction kinetics stereospecificity (Chemical Equation Presented) Herein we report a study involving the homogeneous catalytic reduction of unsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media. © 2008 American Chemical Society. Fil:Gaviglio, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Doctorovich, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v73_n14_p5379_Gaviglio http://hdl.handle.net/20.500.12110/paper_00223263_v73_n14_p5379_Gaviglio
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Chemical reactions Hydrogen Iron Nonmetals Olefins Organic compounds Organic solvents Aqueous solutions Catalytic amounts Catalytic reductions Chemical equations Water-organic solvent mixtures Solutions alkene derivative carbon hydrogen isotope organic solvent water aqueous solution article catalysis chemical reaction cost kinetics pressure reduction kinetics stereospecificity
spellingShingle	Chemical reactions Hydrogen Iron Nonmetals Olefins Organic compounds Organic solvents Aqueous solutions Catalytic amounts Catalytic reductions Chemical equations Water-organic solvent mixtures Solutions alkene derivative carbon hydrogen isotope organic solvent water aqueous solution article catalysis chemical reaction cost kinetics pressure reduction kinetics stereospecificity Gaviglio, Carina Del Valle Doctorovich, Fabio Ariel Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
topic_facet	Chemical reactions Hydrogen Iron Nonmetals Olefins Organic compounds Organic solvents Aqueous solutions Catalytic amounts Catalytic reductions Chemical equations Water-organic solvent mixtures Solutions alkene derivative carbon hydrogen isotope organic solvent water aqueous solution article catalysis chemical reaction cost kinetics pressure reduction kinetics stereospecificity
description	(Chemical Equation Presented) Herein we report a study involving the homogeneous catalytic reduction of unsaturated substrates in aqueous solutions or water-organic solvent mixtures. The reduction of olefins has been carried out in the presence of catalytic amounts of [Fe(CN)5NH3] 3- and excess of NH2OH, which under mild reaction conditions can be used to reduce carbon-carbon unsaturations without affecting carbonyl functionalities and aromatic rings. To explore the scope of the catalytic reduction, a wide variety of representative unsaturated substrates have been examined. The steric effects of the substituents on the carbon-carbon multiple bond as well as the regioselectivity and stereoselectivity of the catalyst have been studied. The deuterium kinetic isotope effect on the catalytic reduction of double bonds in olefins has been analyzed, and no significant kinetic isotope effect was found. Among the great advantages of this novel procedure for catalytic reduction are that hydrogen and high pressures are not needed, the catalyst is inexpensive and easily prepared, and water as well as water-organic solvent mixtures can be used as reaction media. © 2008 American Chemical Society.
author	Gaviglio, Carina Del Valle Doctorovich, Fabio Ariel
author_facet	Gaviglio, Carina Del Valle Doctorovich, Fabio Ariel
author_sort	Gaviglio, Carina Del Valle
title	Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
title_short	Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
title_full	Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
title_fullStr	Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
title_full_unstemmed	Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
title_sort	hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions
publishDate	2008
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v73_n14_p5379_Gaviglio http://hdl.handle.net/20.500.12110/paper_00223263_v73_n14_p5379_Gaviglio
work_keys_str_mv	AT gavigliocarinadelvalle hydrogenfreehomogeneouscatalyticreductionofolefinsinaqueoussolutions AT doctorovichfabioariel hydrogenfreehomogeneouscatalyticreductionofolefinsinaqueoussolutions
_version_	1768542678755049472

Hydrogen-free homogeneous catalytic reduction of olefins in aqueous solutions

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