Oxidative synthesis of azacyclic derivatives through the nitrenium ion: application of a hypervalent iodine species electrochemically generated from iodobenzene

Amano, Yoshiharu; Nishiyama, Shigeru

doi:10.1016/j.tetlet.2006.07.050

Cited by 77 publications

(39 citation statements)

References 17 publications

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“…[962][963][964][965][966][967][968][969] In this context, hypervalent iodine species electrochemically generated from the corresponding iodoarenes have been applied for the synthesis of various heterocyclic frameworks, such as carbazoles 970 (Scheme 127), pyrroloindoles, 971 quinolinone derivatives 972 (Scheme 128) and spirocycles (Scheme 129). 973,974 The utility of electrochemically generated hypervalent iodine reagents has also been demonstrated in the synthesis of glycozoline 970 and tetrahydropyrroloiminoquinone alkaloids. 975,976 The supporting electrolyte has also been merged with the iodine mediator through tethering of the redox-active iodophenyl moiety to an alkylammonium moiety.…”

Section: Electrochemical Generation Of Nitrogen-centered Radicalsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Section: Electrochemical Generation Of Nitrogen-centered Radicalsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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“…Recently, Luo and co-workers elegantly developed catalytic asymmetric oxidative coupling of tertiary amines with alkyl ketones via the combination of electrochemical oxidation and chiral primary amine catalysis (Scheme 14). [19] Simple ketones such as…”

Section: Alkane C-h Functionalizationmentioning

confidence: 99%

Recent Advances in Organic Electrochemical C—H Functionalization

2018

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Organic electrochemistry has a rich history in organic synthesis and has been considered as a promising alternative to traditional chemical oxidants and reductants because it obviates the use of stoichiometric amount of dangerous and toxic reagents. In particular, the electrochemical C—H bonds functionalization is one of the most desirable approaches for the construction of carbon–carbon (C—C) and carbon–heteroatom (C—X) bonds. This review summarizes the substantial progress made in the last few years in C—H functionalization via organic electrochemistry. It is divided into sections on C—C, C—N, C—O, C—S, C–Halogen and C—P bond formation.

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“…The iodine(III) speciesg enerated from iodobenzene provedt ob et he most powerful oxidant in this series, where it leads to the formation of 32 in almost quantitative yield (97 %) being even superior than [bis(trifluoroacetoxy)iodo]benzene (84 %yield). [67] Similarly,t he phenolic dearomatization/spirolactamization of the methoxyamide derivatives 33 was achievedi nh igh yields using the electrochemically generated 30 (Scheme 12), [68] which againp roved to be comparable or superior to direct anodic oxidation and [bis(trifluoroacetoxy)iodo)benzene. The spirocyclic products 34 were obtained exclusively when the substituent Ri sh ydrogen or halogen, while in the case of strong electron-donating substituents (R = OMe) the reaction was unselective and gave amixture of 34 and 35 in an approximately 1:1ratio.…”

Section: Oxidative Heterocyclizationsmentioning

confidence: 99%

“…Oxidationoft he methoxyamidederivatives 33. [68] Scheme13. Oxidationoft he methoxyamide derivatives 36 and 39.…”

Section: Oxidative Heterocyclizationsmentioning

confidence: 99%

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Hypervalent Iodine Reagents by Anodic Oxidation: A Powerful Green Synthesis

Elsherbini

Wirth

2018

Chemistry A European J

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The anodic oxidation of aryl iodides is a powerful method for the synthesis of hypervalent iodine reagents, which eliminates the necessity to use expensive or hazardous chemical oxidizing reagents. The hypervalent iodine reagents generated at the anode are successfully used as either in-cell or ex-cell mediators for different valuable chemical transformations such as fluorinations and oxidative cyclizations. More recently, recyclable mediators and catalytic protocols have been developed.

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Oxidative synthesis of azacyclic derivatives through the nitrenium ion: application of a hypervalent iodine species electrochemically generated from iodobenzene

Cited by 77 publications

References 17 publications

Electrochemical strategies for C–H functionalization and C–N bond formation

Electrochemical strategies for C–H functionalization and C–N bond formation

Recent Advances in Organic Electrochemical C—H Functionalization

Hypervalent Iodine Reagents by Anodic Oxidation: A Powerful Green Synthesis

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