دورية أكاديمية
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Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.

التفاصيل البيبلوغرافية
العنوان: Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.
المؤلفون: Murray PRD; Department of Chemistry, Princeton University, Princeton, New Jersey08544, United States., Leibler IN; Department of Chemistry, Princeton University, Princeton, New Jersey08544, United States., Hell SM; Department of Chemistry, Princeton University, Princeton, New Jersey08544, United States., Villalona E; Department of Chemistry, Princeton University, Princeton, New Jersey08544, United States., Doyle AG; Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California90095, United States., Knowles RR; Department of Chemistry, Princeton University, Princeton, New Jersey08544, United States.
المصدر: ACS catalysis [ACS Catal] 2022 Nov 04; Vol. 12 (21), pp. 13732-13740. Date of Electronic Publication: 2022 Oct 26.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 101562209 Publication Model: Print-Electronic Cited Medium: Print ISSN: 2155-5435 (Print) NLM ISO Abbreviation: ACS Catal Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Washington, DC : American Chemical Society, c2011-
مستخلص: We introduce here a two-component annulation strategy that provides access to a diverse collection of five- and six-membered saturated heterocycles from aryl alkenes and a family of redox-active radical precursors bearing tethered nucleophiles. This transformation is mediated by a combination of an Ir(III) photocatalyst and a Brønsted acid under visible-light irradiation. A reductive proton-coupled electron transfer generates a reactive radical which undergoes addition to an alkene. Then, an oxidative radical-polar crossover step leading to carbocation formation is followed by ring closure through cyclization of the tethered nucleophile. A wide range of heterocycles are easily accessible, including pyrrolidines, piperidines, tetrahydrofurans, morpholines, δ-valerolactones, and dioxanones. We demonstrate the scope of this approach through broad structural variation of both reaction components. This method is amenable to gram-scale preparation and to complex fragment coupling.
Competing Interests: The authors declare no competing financial interest.
(© 2022 The Authors. Published by American Chemical Society.)
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تواريخ الأحداث: Date Created: 20221111 Latest Revision: 20221112
رمز التحديث: 20221213
مُعرف محوري في PubMed: PMC9638994
DOI: 10.1021/acscatal.2c04316
PMID: 36366762
قاعدة البيانات: MEDLINE
الوصف
تدمد:2155-5435
DOI:10.1021/acscatal.2c04316