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- Publisher Website: 10.1021/acs.orglett.9b03578
- Scopus: eid_2-s2.0-85074712646
- PMID: 31668078
- WOS: WOS:000497259500074
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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
Title | Halogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes |
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Authors | |
Keywords | Chalcogens Spin-Spin Coupling Hydrogen Bonds |
Issue Date | 2019 |
Publisher | American 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? |
Abstract | The 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 Identifier | http://hdl.handle.net/10722/290120 |
ISSN | 2023 Impact Factor: 4.9 2023 SCImago Journal Rankings: 1.245 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | LIU, X | - |
dc.contributor.author | MA, S | - |
dc.contributor.author | Toy, PH | - |
dc.date.accessioned | 2020-10-22T08:22:23Z | - |
dc.date.available | 2020-10-22T08:22:23Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Organic Letters, 2019, v. 21 n. 22, p. 9212-9216 | - |
dc.identifier.issn | 1523-7060 | - |
dc.identifier.uri | http://hdl.handle.net/10722/290120 | - |
dc.description.abstract | The 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.language | eng | - |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html | - |
dc.relation.ispartof | Organic Letters | - |
dc.rights | This 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.subject | Chalcogens | - |
dc.subject | Spin-Spin Coupling | - |
dc.subject | Hydrogen Bonds | - |
dc.title | Halogen Bond-Catalyzed Friedel–Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes | - |
dc.type | Article | - |
dc.identifier.email | Toy, PH: phtoy@hkucc.hku.hk | - |
dc.identifier.authority | Toy, PH=rp00791 | - |
dc.description.nature | postprint | - |
dc.identifier.doi | 10.1021/acs.orglett.9b03578 | - |
dc.identifier.pmid | 31668078 | - |
dc.identifier.scopus | eid_2-s2.0-85074712646 | - |
dc.identifier.hkuros | 315936 | - |
dc.identifier.volume | 21 | - |
dc.identifier.issue | 22 | - |
dc.identifier.spage | 9212 | - |
dc.identifier.epage | 9216 | - |
dc.identifier.isi | WOS:000497259500074 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 1523-7052 | - |