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Article: Halogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes

TitleHalogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes
Authors
LIU, XMA, SToy, PH
KeywordsChalcogens
Spin-Spin Coupling
Hydrogen Bonds
Issue Date2019
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2019, v. 21 n. 22, p. 9212-9216 How to Cite?
DOI: http://dx.doi.org/10.1021/acs.orglett.9b03578
AbstractThe use of a halogen bond donor to catalyze Friedel–Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.
Persistent Identifierhttp://hdl.handle.net/10722/290120
ISSN
1523-7060
2021 Impact Factor: 6.072
2020 SCImago Journal Rankings: 1.940
ISI Accession Number ID
WOS:000497259500074

 

DC FieldValueLanguage
dc.contributor.authorLIU, X-
dc.contributor.authorMA, S-
dc.contributor.authorToy, PH-
dc.date.accessioned2020-10-22T08:22:23Z-
dc.date.available2020-10-22T08:22:23Z-
dc.date.issued2019-
dc.identifier.citationOrganic Letters, 2019, v. 21 n. 22, p. 9212-9216-
dc.identifier.issn1523-7060-
dc.identifier.urihttp://hdl.handle.net/10722/290120-
dc.description.abstractThe use of a halogen bond donor to catalyze Friedel–Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html-
dc.relation.ispartofOrganic Letters-
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 https://pubs.acs.org/doi/10.1021/acs.orglett.9b03578-
dc.subjectChalcogens-
dc.subjectSpin-Spin Coupling-
dc.subjectHydrogen Bonds-
dc.titleHalogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes-
dc.typeArticle-
dc.identifier.emailToy, PH: phtoy@hkucc.hku.hk-
dc.identifier.authorityToy, PH=rp00791-
dc.description.naturepostprint-
dc.identifier.doi10.1021/acs.orglett.9b03578-
dc.identifier.pmid31668078-
dc.identifier.scopuseid_2-s2.0-85074712646-
dc.identifier.hkuros315936-
dc.identifier.volume21-
dc.identifier.issue22-
dc.identifier.spage9212-
dc.identifier.epage9216-
dc.identifier.isiWOS:000497259500074-
dc.publisher.placeUnited States-
dc.identifier.issnl1523-7052-

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