Synthesis of nitriles by catalytic dehydrogenation of amines using ruthenium complexes
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Synthesis of nitriles by catalytic dehydrogenation of amines using ruthenium complexesAutoría
Tutor/Supervisor
Mata Martínez, José AntonioTutor/Supervisor; Universidad.Departamento
Universitat Jaume I. Departament de Química Inorgànica i OrgànicaFecha de publicación
2014Editor
Universitat Jaume IResumen
Nitriles represent one of the most important classes of organic compounds used as
intermediates in the synthesis of biologically active compounds and pharmaceutical
substances. Furthermore, they are also used in ... [+]
Nitriles represent one of the most important classes of organic compounds used as
intermediates in the synthesis of biologically active compounds and pharmaceutical
substances. Furthermore, they are also used in agrochemicals, herbicides, polymers,
dyes and natural products, which are derived from amino acids in plants, arthropods,
bacteria and fungi. Nitriles are also versatile intermediates in synthetic organic
chemistry due to their easy conversion into amines, amides, carboxylic acids,
aldehydes, esters, etc. The most common and well-known procedure for the preparation of nitriles is the
nucleophilic displacement of substrates with suitable leaving groups such as halogen
compounds, aryl sulphonates, alcohols, ester, ethers, nitro or amino compounds and
diazonium salts with inorganic cyanide ions. The conventional methods and several other reported procedures such as dehydration of amides and aldoximes, condensation of carboxylic acids with NH3 and
conversion of aldehydes, alcohols and esters, often require hazardous reagents,
severe reaction conditions and/or produce stoichiometric waste. For example, the Rosenmund-von Braun and the Sandmeyer reaction require the use of stoichiometric
amounts of CuCN and produce high amounts of CuCl as waste. To
overcome some of these environmental related problems, catalytic methods such as
direct conversion of primary amines to nitriles via dehydrogenation could be a viable
alternative and clean route if a simple olefin is used as hydrogen acceptor. This
procedure offers a mechanistically distinct and relatively benign pathway for nitrile
synthesis. n catalysis, ruthenium complexes have been proved to be very efficient for transfer
hydrogenation reactions. So considering this previous background, my work has
been focused in the study of the catalytic mechanism of dehydrogenation of amines
into the corresponding nitriles using different ruthenium complexes as catalysts. For
that, I have synthesized 3 ruthenium complexes containing NHC ligands
(imidazolylidenes in this case) with different electronic properties. The modulation of
the electronic properties is introduced by changing the functional groups at 4 and 5
positions in the imidazol ring. The main purpose of this work was to study how the electronic density over the
metal affects the effectiveness of the dehydrogenation of amines over a series of
arenes with different functional groups. [-]
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Treball Final de Grau en Química. Codi: QU0943. Curs: 2014/2015
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- Grau en Química [265]