One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

Handle URI:
http://hdl.handle.net/10754/583936
Title:
One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere
Authors:
Wang, Xinbo; Pan, Yupeng; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Lai, Zhiping ( 0000-0001-9555-6009 )
Abstract:
A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.
KAUST Department:
Physical Sciences and Engineering (PSE) Division
Citation:
One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere 2015, 17 (22):5630 Organic Letters
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
Issue Date:
6-Nov-2015
DOI:
10.1021/acs.orglett.5b02881
Type:
Article
ISSN:
1523-7060; 1523-7052
Is Supplemented By:
Wang, X., Pan, Y., Huang, K.-W., & Lai, Z. (2015). CCDC 1438644: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1k90wr; DOI:10.5517/cc1k90wr; HANDLE:http://hdl.handle.net/10754/624487
Additional Links:
http://pubs.acs.org/doi/10.1021/acs.orglett.5b02881
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorWang, Xinboen
dc.contributor.authorPan, Yupengen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorLai, Zhipingen
dc.date.accessioned2015-12-15T09:28:26Zen
dc.date.available2015-12-15T09:28:26Zen
dc.date.issued2015-11-06en
dc.identifier.citationOne-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere 2015, 17 (22):5630 Organic Lettersen
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.doi10.1021/acs.orglett.5b02881en
dc.identifier.urihttp://hdl.handle.net/10754/583936en
dc.description.abstractA facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.en
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/10.1021/acs.orglett.5b02881en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/10.1021/acs.orglett.5b02881.en
dc.titleOne-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphereen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalOrganic Lettersen
dc.eprint.versionPost-printen
dc.contributor.institutionLaboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, Chinaen
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)en
kaust.authorWang, Xinboen
kaust.authorPan, Yupengen
kaust.authorHuang, Kuo-Weien
kaust.authorLai, Zhipingen
dc.relation.isSupplementedByWang, X., Pan, Y., Huang, K.-W., & Lai, Z. (2015). CCDC 1438644: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1k90wren
dc.relation.isSupplementedByDOI:10.5517/cc1k90wren
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624487en
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