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Article: Highly chemoselective reductive amination of carbonyl compounds promoted by InCl3/Et3SiH/MeOH system

TitleHighly chemoselective reductive amination of carbonyl compounds promoted by InCl3/Et3SiH/MeOH system
Authors
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2008, v. 73 n. 22, p. 8829-8837 How to Cite?
Abstract(Chemical Equation Presented) A new strategy has been developed for reductive amination of aldehydes and ketones with the InCVEt3SiH/MeOH system, which is a nontoxic system with highly chemoselective and nonwater sensitive properties. The methodology can be applied to a variety of cyclic, acyclic, aromatic, and aliphatic amines. Functionalities including ester, hydroxyl, carboxylic acid, and olefin are found to be stable under our conditions. The reaction shows a first-order kinetics profile with respect to both InCl3 and Et3SiH. Spectroscopic techniques such as NMR and ESI-MS have been employed to probe the active and resulting species arising from InCl3 and Et3SiH in MeOH, which are important in deriving a mechanistic proposal. In the ESI-MS studies, we have first discovered the existence of stable methanol-coordinated indium(III) species which are presumably responsible for the gentle generation of indium hydride at room temperature. The solvent attribution was crucial in tuning the reactivity of [In-H] species, leading to the establishment of mild reaction conditions. The system is superior in flexible tuning of hydride reactivity, resulting in the system being highly chemoselective. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168345
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLee, OYen_US
dc.contributor.authorLaw, KLen_US
dc.contributor.authorHo, CYen_US
dc.contributor.authorYang, Den_US
dc.date.accessioned2012-10-08T03:17:50Z-
dc.date.available2012-10-08T03:17:50Z-
dc.date.issued2008en_US
dc.identifier.citationJournal Of Organic Chemistry, 2008, v. 73 n. 22, p. 8829-8837en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/168345-
dc.description.abstract(Chemical Equation Presented) A new strategy has been developed for reductive amination of aldehydes and ketones with the InCVEt3SiH/MeOH system, which is a nontoxic system with highly chemoselective and nonwater sensitive properties. The methodology can be applied to a variety of cyclic, acyclic, aromatic, and aliphatic amines. Functionalities including ester, hydroxyl, carboxylic acid, and olefin are found to be stable under our conditions. The reaction shows a first-order kinetics profile with respect to both InCl3 and Et3SiH. Spectroscopic techniques such as NMR and ESI-MS have been employed to probe the active and resulting species arising from InCl3 and Et3SiH in MeOH, which are important in deriving a mechanistic proposal. In the ESI-MS studies, we have first discovered the existence of stable methanol-coordinated indium(III) species which are presumably responsible for the gentle generation of indium hydride at room temperature. The solvent attribution was crucial in tuning the reactivity of [In-H] species, leading to the establishment of mild reaction conditions. The system is superior in flexible tuning of hydride reactivity, resulting in the system being highly chemoselective. © 2008 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.titleHighly chemoselective reductive amination of carbonyl compounds promoted by InCl3/Et3SiH/MeOH systemen_US
dc.typeArticleen_US
dc.identifier.emailLee, OY:leeonyi@hku.hken_US
dc.identifier.emailYang, D:yangdan@hku.hken_US
dc.identifier.authorityLee, OY=rp00725en_US
dc.identifier.authorityYang, D=rp00825en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo8016082en_US
dc.identifier.pmid18939879-
dc.identifier.scopuseid_2-s2.0-56449127282en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-56449127282&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume73en_US
dc.identifier.issue22en_US
dc.identifier.spage8829en_US
dc.identifier.epage8837en_US
dc.identifier.isiWOS:000260923000018-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLee, OY=7103020334en_US
dc.identifier.scopusauthoridLaw, KL=7202563094en_US
dc.identifier.scopusauthoridHo, CY=35310593500en_US
dc.identifier.scopusauthoridYang, D=7404800756en_US

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