Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

Chan, Chun Ming; Xing, Qi; Chow, Yip Chi; Hung, Sing Fung; Yu, Wing‐Yiu

doi:10.1021/acs.orglett.9b03020

Cited by 40 publications

(27 citation statements)

References 83 publications

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“…Yu and co‐workers showed that the alkyl radicals generated from NHPI esters can also undergo addition to α‐diazo compounds to afford hydrazones (Scheme 89). [373] The reaction employs the organic dye Rose Bengal as photocatalyst and requires the presence of Hantzsch ester as a hydrogen source and an electron donor.…”

Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

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Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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“…In 2019, Yu's group [155] employed rose bengal (RB) as a 有机化学综述与进展 photocatalyst to synthesize various N-alkyl hydrazones 73 in excellent yields through the C(sp 3 )-N coupling between α-diazoacetates 72 and alkyl NHP esters 1 (Scheme 37).…”

Section: Reactions Involving Other Metal-free Organic Dyesmentioning

confidence: 99%

Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions

He¹,

Li²,

Chen³

et al. 2021

Chinese Journal of Organic Chemistry

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N-Hydroxyphthalimide (NHP) esters are easily available, stable, inexpensive, and highly photoactive compounds, which are derived from the corresponding carboxylic acids. In recent years, the application of NHP esters in photocatalytic decarboxylative reactions has captured huge attention. Herein, the vigorous development of photocatalytic alkylation reactions using alkyl NHP esters as alkylating reagents is summarized based on the classification of photocatalysts.

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“…Radical reactions of diazo compounds have also been employed for the assembly of hydrazones with subsequent cyclization to 1,2,4-triazoles. Chan and co-workers developed a photoredox decarboxylative C(sp 3 )−N coupling of N -hydroxyphthalimide (NHPI) esters with α -diazoacetates 406 for the synthesis of hydrazones [ 204 ]. When N -acetyl amino acids derived NHPI esters 405 were used, the initially formed hydrazones 102A underwent cyclization to give 1,2,4-triazoles 407 in good yields.…”

Section: Azoles With Three Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

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Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

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Photoredox Decarboxylative C(sp³)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

Cited by 40 publications

References 83 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

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