Atom transfer radical cyclization reactions (ATRC): synthetic applications

Edlin, Chris D.; Faulkner, James; Helliwell, Madeleine; Knight, Christopher K.; Parker, Jeremy S.; Quayle, Peter; Raftery, James

doi:10.1016/j.tet.2006.01.038

Cited by 28 publications

(5 citation statements)

References 64 publications

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“…Stereoselective cyclization of the trichloro ester derivative 29 furnished 31 in 78 % yield via a sterically controlled atom transfer with intermediate radical 30 being trapped on the face opposite the lactone (Scheme ) 30. A similar approach has been reported for the synthesis of cyclolignans 31…”

Section: Copper Catalyzed Atrcmentioning

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: Copper Catalyzed Atrcmentioning

confidence: 99%

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

Clark

2016

Eur J Org Chem

131

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“…[42] Among them ATRC reactions have provided access to 2-oxabicyclo[4.3.0]nonanes present in terpenes such as eunicellin (Scheme 9 a) or functionalized -butyrolactones (Scheme 9 b). One interesting feature of these reactions is that the products display several halogenated carbon centers that can be subsequently functionalized (Scheme 10).…”

Section: Synthetic Applicationsmentioning

confidence: 99%

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

2011

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Transition‐metal‐catalyzed atom transfer radical reactions of halogenated compounds with olefins constitute a versatile tool in organic synthesis within the area of C–C bond forming transformations. The inter‐ or intramolecular versions, atom transfer radical addition (ATRA) or cyclization (ATRC), respectively, lead to the atom‐economic, useful synthesis of compounds that can be further functionalized. This contribution summarizes the recent developments in this area in terms of catalyst design as well as the applicability of this methodology in sequential, domino, or tandem reactions.

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“…The functionalization of olefins can not only introduce polyhaloalkyl groups and halogens, but also introduce other functional groups such as ethers and azides, and also construct various cyclic compounds by intramolecular cyclization. A well‐known processes are the atom transfer radical addition (ATRA) [3a,9a–e] and cyclization (ATRC), [3b,9f–g] which are usually constructed a carbon‐carbon bond and carbon‐halogen bond by transition metal catalyzed or photoredox catalyzed.…”

Section: Polychloroalkylation Of Alkenesmentioning

confidence: 99%

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

Liang

Ouyang

et al. 2020

Adv Synth Catal

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Owing to their easy availability and cheapness, simple alkyl chlorides are good raw materials for introducing complex polychlorinated groups. Polychlorinated hydrocarbons units, such as di‐ or trichloromethyl groups, not only widely found in pesticide and bioactive molecule, but also can be as a precursor to converted into different functional groups such as −COOH, −CHO and −CO. The direct polychloroalkylation reaction by using simple alkyl chlrides has been considered to be an important tool for synthesizing complex polychlorinated compounds. This review summarizes recent developments, especially free radical strategies, in the polychloroalkylation of different substrates (such as 2‐acylpyridines, benzyl tertiary amines, alkenes, imine and 1,n‐enynes). We hope that this review provides a new perspective on this field and also provides a reference to develop environmentally friendly and sustainable methods.

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Atom transfer radical cyclization reactions (ATRC): synthetic applications

Cited by 28 publications

References 64 publications

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

Atom Transfer Radical Reactions as a Tool for Olefin Functionalization – On the Way to Practical Applications

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

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