Visible light photoredox atom transfer Ueno–Stork reaction

Gu, Xiangyong; Lü, Ping; Fan, Wenbing; Li, Pixu; Yao, Yingming

doi:10.1039/c3ob41600c

Cited by 18 publications

(11 citation statements)

References 57 publications

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“…ATRC is the intramolecular version of ATRA and is attractive synthetically because the halogen (X) is retained, which allows post‐cyclization functionalization if required 3c,6,7. Copper6 and ruthenium catalysts3g,8a–8c are most commonly employed, although iron,9 palladium10 and iridium11 have also been investigated.…”

Section: Introductionmentioning

confidence: 99%

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

Clark

2016

Eur J Org Chem

131

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Atom transfer radical cyclization (ATRC) is a powerful technique to prepare functionalized 4–10 membered ring systems using transition metal catalysts. In this review recent advances in the use of copper complexes are described. In particular the effect of different ligands on reactivity, selectivity and product outcome are illustrated with application to heterocycle and natural product synthesis. New approaches that increase catalyst efficiency with supplemental reducing agents are reviewed and examples using green solvents, benign reducing agents (e.g. ascorbic acid) and with catalyst loadings as low as 0.05 mol‐% are highlighted. Radical addition to aromatic rings and rearrangement reactions under ATRC conditions as well as application to radical‐polar crossover reactions are also described.

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Section: Introductionmentioning

confidence: 99%

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

Clark

2016

Eur J Org Chem

131

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“…In recent years, atom economy was recognized as an important parameter to evaluate the overall efficiency of a chemical process. Various of new methodologies with high atom economy were developed by the organic chemists (Scheme a). For examples, Lautens et al .…”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, atom/group transfer radical cyclization (ATRC or GTRC) was recognized as a powerful method for the formation of ring systems, which are characterized by 100% atom efficiency (Scheme c). Ruthenium and copper catalysts are most commonly employed, although palladium, iridium, iron and Lewis acid have also been investigated. For instance, Cook and co‐workers developed an iodine‐transfer radical cyclization reaction for the formation of primary iodides with concomitant creation of a bicyclic ring.…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Group‐Transfer Radical Cyclization of γ,δ‐Unsaturated Oxime Esters: Synthesis of Ester‐Functionalized Pyrrolines

et al. 2019

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We have realized an atom-economical reaction for the synthesis of ester-functionalized pyrrolines via a copper-catalyzed group-transfer radical cyclization of γ,δunsaturated oxime esters, during which a new CÀ N bond, a new CÀ O bond and a five-membered ring were formed in one step. By using this protocol, a sequence of structurally diversiform acyloxyl-substituted pyrrolines bearing a quaternary carbon center were obtained in moderate to good yields (35-95%).

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“…In 2013, Yao and Li introduced an approach to synthesize oxabicyclic frameworks via visible light photocatalysis (Scheme 11). 21 The reaction of allylic a-iodoacetal, using DIEA as an electron donor and Ir(ppy) 2 (dtbbpy)(PF 6 ) as a photocatalyst under the irradiation of 14 W CFL gave the alkyl iodides in 58-94% yields. Using piperidine instead of tetrahydropyran, the similar reaction could undergo smoothly to afford the [6,5]bicyclic ring product in 94% yield.…”

Section: +mentioning

confidence: 99%