Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives.

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Abstrakt

Tytuł:: Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives.
Autorzy:: Song C; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Liu K; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Jiang X; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Dong X; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Weng Y; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Chiang CW; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.
Lei A; College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China.
Źródło:: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Apr 27; Vol. 59 (18), pp. 7193-7197. Date of Electronic Publication: 2020 Mar 10.
Typ publikacji:: Journal Article; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
MeSH Terms:: Electrochemical Techniques*
Alkaloids/*chemical synthesis
Indoles/*chemistry
Alkaloids/chemistry ; Free Radicals/chemical synthesis ; Free Radicals/chemistry ; Hydrogenation ; Molecular Structure ; Oxidation-Reduction
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Contributed Indexing:: Keywords: [4+2] annulation; dearomative annulation; electrosynthesis; indole; pyrimido[5,4-b]indoles
Substance Nomenclature:: 0 (Alkaloids)
0 (Free Radicals)
0 (Indoles)
Entry Date(s):: Date Created: 20200220 Date Completed: 20210312 Latest Revision: 20210312
Update Code:: 20221216
DOI:: 10.1002/anie.202000226
PMID:: 32073715
: Czasopismo naukowe

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Dearomative annulation of indoles has emerged as a powerful tool for the preparation of polycyclic indoline-based alkaloids. Compared with well-established methods towards five-membered-ring-fused indolines, the six-membered-ring-fused indolines are rarely accessed under thermal conditions. Herein, a dearomative [4+2] annulation between different indoles is developed through an electrochemical pathway. This transformation offers a remarkably regio- and stereoselective route to highly functionalized pyrimido[5,4-b]indoles under oxidant- and metal-free conditions. Notably, this electrochemical approach maintains excellent functional-group tolerance and can be extended as a modification tactic for pharmaceutical research. Preliminary mechanism studies indicate that the electrooxidation annulation proceeds through radical-radical cross-coupling between an indole radical cation and an N-centered radical generated in situ.
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