Synthesis of Difluoromethyl‐Containing α‐Acyloxycarboxamide Derivatives through a Passerini Reaction and Desulfonylation

Zhao, Wenwen; Cao, Song

doi:10.1002/ejoc.201101518

Cited by 10 publications

(1 citation statement)

References 38 publications

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“…Selectivity, synthetic convergency, and atom economy are all benefits of the most useful MCRs. [18,19,20] One such MCR is the well-studied Passerini reaction, however, when performed using ketones it is often slow, and in some situations, reactions with bulky carbonyl substrates and bulky isocyanides do not work at all or fail to provide the desired product. [21,22] In the context of Passerini reactions of sterically hindered carbonyl compounds, we postulated that a multicomponent reaction combining isatin derivatives, isocyanides, and carboxylic acids could allow access to oxindole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Water‐Assisted Passerini Reactions under Mechanochemical Activation: A Simple and Straightforward Access to Oxindole Derivatives

2023

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A protocol based on the Passerini Multi-Component reaction (MCR) has been developed for facile, efficient, environmentally benign and atom economical synthesis of a small library of biologically important oxindole derivatives employing isatin, benzoic acid and substituted isocyanides. In contrast to the conventional approach, which requires the use of toxic organic solvents, Passerini reactions were completed in 10-15 minutes under mechanochemical conditions with excellent yields. The protocol described below allows the modular synthesis of diverse compounds under green chemistry principles, specifically in favourable environmental conditions, with great atom economy, shorter reaction time, cleaner reactions with improved yields, and experimental simplicity.

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Section: Introductionmentioning

confidence: 99%

Water‐Assisted Passerini Reactions under Mechanochemical Activation: A Simple and Straightforward Access to Oxindole Derivatives

2023

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One‐Pot Oxidative Passerini Reaction of Alcohols Using a Magnetically Recyclable TEMPO under Metal‐ and Halogen‐Free Conditions

Karimi

Farhangi

2013

Adv Synth Catal

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A novel domino oxidative Passerini threecomponent reaction (OP-3CR) has been successfully developed with either primary or secondary alcohols instead of their corresponding aldehydes or ketones by using a recyclable magnetic core-shell nanoparticle supported TEMPO (2,2,6,6-tetramethyl-piperidin-1-oxyl) (MNST, 1). It has been shown that MNST is a highly effective and recyclable catalyst system in the metal-and halogen-free aerobic, oxidative, three-component Passerini reaction. To the best of our knowledge this method can be considered as the first example of a OP-3CR of alcohols under metal-and halogen-free reaction conditions. It should be also noted that there has been no precedent example of oxidative OP-3CR of secondary alcohols to their corresponding a-acyloxy carbox-A C H T U N G T R E N N U N G amides. The catalyst can be magnetically recycled and successfully reused in 14 subsequent reaction cycles with only slight decreases of its catalytic activity.

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Catalytic Asymmetric Construction of Stereogenic Carbon Centers that Feature a gem‐Difluoroalkyl Group

Liu

Zhou

2013

Asian J Org Chem

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gem-Difluoroalkyl groups, characterized as a gem-difluoromethylene group substituted by a hydrogen atom or an alkyl or other functional group, are not only valuable for the modulation of the properties of organic compounds, but are also useful for the synthesis of various fluorine-containing compounds. Currently, the catalytic asymmetric construction of stereogenic carbon centers that feature a gem-difluoroalkyl group is in its infancy. This Focus Review summarizes the latest achievements and discusses the difficulties and challenges in this field. Scheme 1. Structural difference between a CF 3 group and a difluoroalkyl group. FG = functional group. Scheme 2. The presence of gem-difluoroalkyl groups in important compounds. Scheme 13. The catalytic asymmetric addition of TMSCF 2 SO 2 Ph to aldehydes. TBAF = tetrabutylammonium fluoride. Scheme 14. The catalytic asymmetric addition of TMSCF 2 SePh to ketones. Ar = 3,5-(CF 3 ) 2 C 6 H 3 . Scheme 15. The asymmetric hydrogenation of a-CF 2 R ketimines. Bn = benzyl. Scheme 16. The Mannich reaction of a-difluoromethyl aldimines 69.

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Synthesis of Difluoromethyl‐Containing α‐Acyloxycarboxamide Derivatives through a Passerini Reaction and Desulfonylation

Abstract: A series of difluoromethyl-containing α-acyloxycarboxamide derivatives were synthesized through a Passerini reaction of acids, aldehydes, and phenylsulfanyl-protected difluorinated isocyanide followed by meta-chloroperoxybenzoic acid me-

Cited by 10 publications

References 38 publications

Water‐Assisted Passerini Reactions under Mechanochemical Activation: A Simple and Straightforward Access to Oxindole Derivatives

Water‐Assisted Passerini Reactions under Mechanochemical Activation: A Simple and Straightforward Access to Oxindole Derivatives

One‐Pot Oxidative Passerini Reaction of Alcohols Using a Magnetically Recyclable TEMPO under Metal‐ and Halogen‐Free Conditions

Catalytic Asymmetric Construction of Stereogenic Carbon Centers that Feature a gem‐Difluoroalkyl Group

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