N-Chlorosuccinimide (NCS)–N,N-dimethylformamide (DMF), a reagent for the oxidation of benzylic alcohols to aldehydes and ketones

Kulkarni, Mahesh R.; Lad, Nitin P.; Gaikwad, Nitin D.

doi:10.1007/s11030-019-09954-3

Cited by 7 publications

(6 citation statements)

References 19 publications

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“…By further control experiments, literature evidences, 22 and theoretical investigations, a plausible mechanism for photoinitiated aldehyde ( 1 ) generation from benzylidenemalononitrile ( 3 ) is proposed as shown in Scheme 8. For theoretical investigation of the reaction mechanism, 2-benzylidenemalononitrile ( 1a ) was taken as a model compound (Fig.…”

Section: Resultsmentioning

confidence: 99%

Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer

Das

Thomas

2023

Green Chem.

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Section: Resultsmentioning

confidence: 99%

Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer

Das

Thomas

2023

Green Chem.

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“…Traditional oxidation methods (Figure 7) have several drawbacks like the use of hazardous peroxides, metal catalysts, and the use of elevated reaction temperature Gaikwad [ 59 ] group developed, catalyst‐free, toxic metal‐free oxidation of alcohols with simple, mild reaction conditions using NCS‐DMF at rt, with less reaction time afforded corresponding carbonyl compounds in excellent yields (Scheme 27).…”

Section: Oxidative Transformations (C–cl and C–o)mentioning

confidence: 99%

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Govada

Reddy

2022

Applied Organom Chemis

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Owing to their various modes of coordinating and oxidizing reactivity, organic chloramines represent versatile building blocks for the synthesis of an ample range of multiatomic organic compounds. The present review focuses on synthetic methodologies using their dichotomous nature, which is the basis of their reactivity as oxidant and substrate. This is the first ever review covering the extensive applications of this large class of N–Cl compounds (organic chloramines) especially using one‐pot reaction strategies for various organic transformations, and construction of bonds such as chlorination (C–Cl, S–Cl), oxidation (C=O), cross‐coupling (C–N, CONR, S–N), cyclization, substitution, rearrangement, and catalysis, have been described, briefly to highlight important aspects of the organic chloramines in organic synthesis.

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“…For example, recently Kulkarni et al developed mild oxidation conditions for the conversion of benzylic alcohols 36 to the corresponding aldehydes and ketones 37 using N-chlorosuccinimide (NCS)/DMF (Scheme 12). 68 This method was demonstrated to give easy access to a wide variety of carbonyl compounds in good yields under metal-free conditions without the use of corrosive reagents.…”

Section: Potential Safety Hazards With Dmfmentioning

confidence: 99%

Potential Safety Hazards Associated with Using N,N-Dimethylformamide in Chemical Reactions

Yang

Sheng

Huang

2020

Org. Process Res. Dev.

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N,N-Dimethylformamide (DMF) is frequently used as a solvent because of its unique physical properties that allow it to solubilize both organic and inorganic substances. It has also found broad applications as a catalyst for a variety of chemical transformations and as a donor for many functional groups in synthetic organic chemistry. However, DMF is incompatible with a wide variety of substances and has resulted in many incidents over the years. Analysis of literature information indicates that those incompatible substances can be categorized as acids, bases, halogenated reagents, oxidants, and reductants. This comprehensive review of the potential hazards of using DMF in chemical reactions will serve as an educational resource to promote awareness of such safety hazards in the broader chemistry community and encourage scientists to develop appropriate control strategies to mitigate the potential safety risks associated with the use of DMF in chemical reactions.

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N-Chlorosuccinimide (NCS)–N,N-dimethylformamide (DMF), a reagent for the oxidation of benzylic alcohols to aldehydes and ketones

Cited by 7 publications

References 19 publications

Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer

Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer

A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines

Potential Safety Hazards Associated with Using N,N-Dimethylformamide in Chemical Reactions

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