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Article: Highly efficient oxidation of amines to imines by singlet oxygen and its application in ugi-type reactions

TitleHighly efficient oxidation of amines to imines by singlet oxygen and its application in ugi-type reactions
Authors
Issue Date2009
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2009, v. 11 n. 20, p. 4568-4571 How to Cite?
AbstractA variety of secondary benzylic amines were oxidized to imines in 90% to >99% yields by singlet oxygen generated from oxygen and a porphyrin photosensitizer. On the basis of these reactions, a protocol was developed for oxidative Ugi-type reactions with singlet oxygen as the oxidant. This protocol has been used to synthesize C1- and N-functionalized benzylic amines in up to 96% yields. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/70059
ISSN
2015 Impact Factor: 6.732
2015 SCImago Journal Rankings: 3.187
ISI Accession Number ID
Funding AgencyGrant Number
The University of Hong Kong
University Grants CouncilAoE 10/01P
Funding Information:

This work was supported by The University of Hong Kong (University Development Fund), the University Grants Council of HKSAR (the Area of Excellence Scheme: AoE 10/01P), the Hong Kong Research Grants Council (HKU7009/06P and CityU 2/06C), and the CAS-Croucher Funding Scheme for Joint Laboratory. We thank Prof. Kuiling Ding (SIOC) for his useful discussion. G.J. and J.C. thank the Croucher Foundation of Hong Kong for a postgraduate studentship.

References

 

DC FieldValueLanguage
dc.contributor.authorJiang, Gen_HK
dc.contributor.authorChen, Jen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:19:20Z-
dc.date.available2010-09-06T06:19:20Z-
dc.date.issued2009en_HK
dc.identifier.citationOrganic Letters, 2009, v. 11 n. 20, p. 4568-4571en_HK
dc.identifier.issn1523-7060en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70059-
dc.description.abstractA variety of secondary benzylic amines were oxidized to imines in 90% to >99% yields by singlet oxygen generated from oxygen and a porphyrin photosensitizer. On the basis of these reactions, a protocol was developed for oxidative Ugi-type reactions with singlet oxygen as the oxidant. This protocol has been used to synthesize C1- and N-functionalized benzylic amines in up to 96% yields. © 2009 American Chemical Society.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_HK
dc.relation.ispartofOrganic Lettersen_HK
dc.subject.meshAmines - chemistry-
dc.subject.meshImines - chemistry-
dc.subject.meshOxidation-Reduction-
dc.subject.meshSinglet Oxygen - chemistry-
dc.titleHighly efficient oxidation of amines to imines by singlet oxygen and its application in ugi-type reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1523-7060&volume=11&issue=20&spage=4568&epage=4571&date=2009&atitle=Highly+efficient+oxidation+of+amines+to+imines+by+singlet+oxygen+and+its+application+in+ugi-type+reactionsen_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ol9018166en_HK
dc.identifier.pmid19810764en_HK
dc.identifier.scopuseid_2-s2.0-70349911749en_HK
dc.identifier.hkuros168982en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-70349911749&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume11en_HK
dc.identifier.issue20en_HK
dc.identifier.spage4568en_HK
dc.identifier.epage4571en_HK
dc.identifier.isiWOS:000270461300022-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridJiang, G=35310477700en_HK
dc.identifier.scopusauthoridChen, J=36047378100en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.citeulike9066997-

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