Facile production and cyclizations of amidyl radicals

Newcomb, Martin; Esker, John L.

doi:10.1016/s0040-4039(00)74480-7

Cited by 70 publications

(21 citation statements)

References 9 publications

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“…Long recognized as valuable synthons for C-N bond formation [203,[208][209][210][211][212][213], these intermediates have not enjoyed widespread application in synthesis because of the inability to access these intermediates directly from native amide N-H bond precursors. The most common methods of amidyl generation typically require N-functionalized amides or the use of strong stoichiometric oxidants to effectively furnish the radical species.…”

Section: Amidesmentioning

confidence: 99%

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Miller

Tarantino

Knowles

2016

Topics in Current Chemistry Collections

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Proton-coupled electron transfers (PCETs) are unconventional redox processes in which both protons and electrons are exchanged, often in a concerted elementary step. While PCET is now recognized to play a central a role in biological redox catalysis and inorganic energy conversion technologies, its applications in organic synthesis are only beginning to be explored. In this chapter we aim to highlight the origins, development and evolution of PCET processes most relevant to applications in organic synthesis. Particular emphasis is given to the ability of PCET to serve as a non-classical mechanism for homolytic bond activation that is complimentary to more traditional hydrogen atom transfer processes, enabling the direct generation of valuable organic radical intermediates directly from their native functional group precursors under comparatively mild catalytic conditions. The synthetically advantageous features of PCET reactivity are described in detail, along with examples from the literature describing the PCET activation of common organic functional groups.

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Section: Amidesmentioning

confidence: 99%

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Miller

Tarantino

Knowles

2016

Topics in Current Chemistry Collections

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“…The amides 3 were converted into the appropriate α-chloroimines by treatment with phosgene and catalytic DMF. 16 We found other methods of preparing the α-chloroimines were unsatisfactory for further reactions. The potassium salt of phenylselanide was prepared in situ by reduction of diphenyl diselanide with K-Selectride ® and added directly to the un-purified α-chloroimines to give the imidoyl-selanides 2 (Scheme 2, Table 1).…”

Section: Resultsmentioning

confidence: 98%

Palladium and radical routes to phenanthridines

Bowman¹,

Lyon²,

Pritchard³

2012

Arkivoc

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“…Так, із аміду 130 че-рез проміжний імідат 131 був генерований амі-дильний радикал А, який в присутності інгібіто-рів радикальних процесів (PhSeSePh, трет-BuSH) зазнає 5-ендо-циклізації і через інтермедіат Б пе-ретворюється на 5-заміщений піролідинон 132 [66,67]. Для генерування попередників амідильних радикалів також знайшли застосування N-ацил-N-алкіл-N′-гідроксипіридин-2-тіони [68] (схема 54).…”

Section: радикальні циклізаціїunclassified

Heterocyclization of amides of alkenylcarboxylic acids

Tsyzoryk¹,

Васькевич²,

Вовк³

2015

J. org. pharm. chem.

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(Ховейда, Граббса, Нолана), реакції мета-тезису, а також радикальних процесів у регіо-та стереоселективних циклізаціях амідів у м'яких умовах. Розглянуті синтетичні варіанти носять загальний характер і дозволяють поряд із процесами циклізації здійснювати спрямовану функціоналізацію O-, N-, S-вмісних малих та середніх гетероциклічних систем. HETEROCYCLIZATION OF AMIDES OF ALKENYLCARBOXYLIC ACIDS N.M.Tsyzoryk, A.I.Vaskevich, M.V.Vovk Key words: amides of alkenylcarboxylic acids; electrophilic intramolecular cyclization; lactones; lactams The latest published data on heterocyclization of amides of alkenylcarboxylic acids have been systematized. It has been proven that the electrophilic intramolecular cyclization reaction of functionally substituted olefins opened in the 70s of the last century is a convenient way of constructing different oxygen-, nitrogen-and sulfurcontaining heterocyclic compounds. It has been noted that anilides of unsaturated carboxylic acids as bifunctional nucleophilic systems containing alkenyl and aminocarbonyl functions are useful models to study the electrophilic cyclization reaction, which leads to formation of O-and N-containing heterocycles (lactones and lactams). The last of them belong to the important types of compounds used as key blocks in the synthesis of biologically active alkaloids and their analogues, pharmaceutical and agrochemical products. The effective approaches to the synthesis of new types of functionalized lactones and lactams have been developed; amides of 3-butenoic, 4-pentenoic and 5-hexenoic acids are often used as substrates for their design. Along with classical methods of synthesis of lactones and lactams the literary sources relating to the use of original catalytic electrophilic systems (Nolan, Grubbs, Hoveyda), the metathesis reaction and radical processes in regio-and stereoselective cyclization of amides under mild conditions have been analyzed and summarized in the article. The synthetic versions considered are general in nature and allow to perform the targeted functionalization of O-, N-, S-containing heterocyclic small and medium-sized systems along with the cyclization processes. ГЕТЕРОЦИКЛИЗАЦИИ АМИДОВ АЛКЕНИЛКАРБОНОВЫХ КИСЛОТ

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Facile production and cyclizations of amidyl radicals

Cited by 70 publications

References 9 publications

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Palladium and radical routes to phenanthridines

Heterocyclization of amides of alkenylcarboxylic acids

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