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Article: Halogen Bond‐Catalyzed Povarov Reactions
Title | Halogen Bond‐Catalyzed Povarov Reactions |
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Authors | |
Keywords | cycloaddition halogen bond organocatalysis Povarov reaction tetrahydroquinolines |
Issue Date | 2020 |
Publisher | Wiley-VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1615-4169 |
Citation | Advanced Synthesis & Catalysis, 2020, v. 362 n. 16, p. 3437-3441 How to Cite? |
Abstract | The use of a bidentate halogen bond donor to catalyse Povarov reactions of imines derived from aryl adehydes and anilines is reported. Dienophiles used in these reactions included 2,3-dihydrofuran, N-vinyl-2-pyrrolidone and N-Cbz-protected 2,3-dihydropyrrole. Very high isolated yields of the desired 1,2,3,4-tetrahydroquinoline products were obtained with low catalyst loadings (0.01 equivalents) and short reaction times (minutes to hours) at ambient temperature. Notably, the bis(benzimidazolium iodide)-based catalyst used in these reactions proved to be more efficient than analogous bromine and chlorine functionalized compounds, as well as a related monodentate benzimidizolium iodide. These observations are similar to what has been reported by others regarding halogen bond organocatalysis, and may prove useful in guiding catalyst design as the field moves forward. |
Persistent Identifier | http://hdl.handle.net/10722/306344 |
ISSN | 2023 Impact Factor: 4.4 2023 SCImago Journal Rankings: 1.020 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | LIU, X | - |
dc.contributor.author | Toy, PH | - |
dc.date.accessioned | 2021-10-20T10:22:18Z | - |
dc.date.available | 2021-10-20T10:22:18Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Advanced Synthesis & Catalysis, 2020, v. 362 n. 16, p. 3437-3441 | - |
dc.identifier.issn | 1615-4150 | - |
dc.identifier.uri | http://hdl.handle.net/10722/306344 | - |
dc.description.abstract | The use of a bidentate halogen bond donor to catalyse Povarov reactions of imines derived from aryl adehydes and anilines is reported. Dienophiles used in these reactions included 2,3-dihydrofuran, N-vinyl-2-pyrrolidone and N-Cbz-protected 2,3-dihydropyrrole. Very high isolated yields of the desired 1,2,3,4-tetrahydroquinoline products were obtained with low catalyst loadings (0.01 equivalents) and short reaction times (minutes to hours) at ambient temperature. Notably, the bis(benzimidazolium iodide)-based catalyst used in these reactions proved to be more efficient than analogous bromine and chlorine functionalized compounds, as well as a related monodentate benzimidizolium iodide. These observations are similar to what has been reported by others regarding halogen bond organocatalysis, and may prove useful in guiding catalyst design as the field moves forward. | - |
dc.language | eng | - |
dc.publisher | Wiley-VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1615-4169 | - |
dc.relation.ispartof | Advanced Synthesis & Catalysis | - |
dc.rights | This is the peer reviewed version of the following article: Advanced Synthesis & Catalysis, 2020, v. 362 n. 16, p. 3437-3441, which has been published in final form at https://doi.org/10.1002/adsc.202000665. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | - |
dc.subject | cycloaddition | - |
dc.subject | halogen bond | - |
dc.subject | organocatalysis | - |
dc.subject | Povarov reaction | - |
dc.subject | tetrahydroquinolines | - |
dc.title | Halogen Bond‐Catalyzed Povarov Reactions | - |
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 | 10.1002/adsc.202000665 | - |
dc.identifier.scopus | eid_2-s2.0-85088129063 | - |
dc.identifier.hkuros | 327363 | - |
dc.identifier.volume | 362 | - |
dc.identifier.issue | 16 | - |
dc.identifier.spage | 3437 | - |
dc.identifier.epage | 3441 | - |
dc.identifier.isi | WOS:000548687100001 | - |
dc.publisher.place | Germany | - |