Recent Advances On Direct Formylation Reactions

Kherudkar, Aditya; Bhattacharjee, Angana; Nawkhare, Akash; Mukherjee, Soumi; Pramanick, Sukhendu; Laha, Joydev K.

doi:10.1002/tcr.202300063

Cited by 6 publications

(2 citation statements)

References 79 publications

(124 reference statements)

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“…There are several methods for achieving formylation Vilsmeier−Haack reaction, Gattermann−Koch reaction, hydroformylation and formylating reagents (ethyl formate, diethylformamide, and formic acid, often used in combination with Lewis acids or bases to facilitate the reaction). Among the other formylating agents, 144 methanol is a desirable formylating agent due to its availability, low cost, and convenience. This section covers the catalytic Nformylation reaction that uses methanol as a formylation reagent through ADC (Figure 7).…”

Section: 2cmentioning

confidence: 99%

Multi-Functionality of Methanol in Sustainable Catalysis: Beyond Methanol Economy

Sivakumar,

Kumar,

Yadav

et al. 2023

ACS Catal.

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Methanol is a fundamental feedstock and is widely used in the chemical and petroleum industries. It can serve as a C1 source to make a variety of C−C and C−N bond formation and dehydrogenative coupling products, which have important applications in natural products and drug discovery. A high hydrogen content (12.5 wt%) of methanol makes it an effective H 2 donor for the transfer hydrogenation of various reducible functional groups. A plethora of various transition metal-based dehydrogenative processes have been developed using methanol. Notably, recent review articles focused on the C1 aspect of methanol. However, a more updated review that examines the challenges and applications of methanol as both a C1-source and H 2 -source in organic transformations contributing to the concept of the methanol economy has not been presented yet. This Review summarizes the transition metal-based (homogeneous, heterogeneous, and photo-) catalyst system for C-, N-, and O-methylation of ketones, alcohols, amides, nitriles, heterocyclic compounds, sulfones, amines, amides, sulfonamides and direct N-methylation of nitro compounds under borrowing hydrogen strategy and N-formylation of amines using methanol under acceptorless dehydrogenation coupling using methanol as a C1 source. It also covers insights into reaction mechanisms and the role of carefully selected ligands in the metal catalysis for methanol activation and incorporation of -CD 3 , methylation of drug molecules. Moreover, it describes transfer hydrogenation of various functional groups such as aldehydes, ketones, alkynes, and nitro with methanol as an H 2 donor in detail.

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Section: 2cmentioning

confidence: 99%

Multi-Functionality of Methanol in Sustainable Catalysis: Beyond Methanol Economy

Sivakumar,

Kumar,

Yadav

et al. 2023

ACS Catal.

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“…A few examples for this type of transformation are radical addition of chloroform by a Grubbs catalyst, followed by dehydrochlorination–hydrolysis (Scheme a), and copper-catalyzed radical hydroxydichloromethylation, followed by dehydrogenation–hydrolysis (Scheme b) . Vilsmeier–Haack formylation, which is classified as a direct formylation, has been applied not only to aromatic compounds but also to alkenes (Scheme c) . However, the formylation reactions of alkenes reported to date are unsatisfactory in terms of substrate scope and/or product yields.…”

mentioning

confidence: 99%

Lewis Acid-Mediated Friedel–Crafts-Type Formylation of Alkenes with Dichloromethyl Methyl Ether in the Presence of Pyridines

Tanaka,

Yoshii,

Hattori

2024

J. Org. Chem.

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Various alkenes are formylated with dichloromethyl methyl ether (MOMCl 2 ) by the combined use of SnCl 4 /2,6dibromopyridine (B1) or AgOTf/pyridine (B4) via Friedel−Craftstype reaction. The former reagent combination is mainly applied to α,α-diarylalkenes, while the latter one is applied not only to arylalkenes but also to some alkylalkenes. Vinyl aldehydes are exclusively obtained from alkenes that can possibly afford both allyl and vinyl aldehydes.

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Enantioselective Construction of Oxindoles Bearing a Quaternary Carbon via Ni−Al Bimetal‐Catalyzed Formyl C−H Alkylation

Wang,

Li,

et al. 2024

Angewandte Chemie

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Enantioselective transition metal‐catalyzed C–H alkylation emerges as one of the most atom‐ and step‐economical routes to chiral quaternary carbons, while big challenges still remain with acyl C–H alkylations. Herein, we use a Ni–Al bimetallic catalyst to facilitate a highly regioselective and highly enantioselective C–H alkylation of formamides with alkenes, constructing various oxindoles bearing a chiral quaternary carbon in up to 94% yield and up to 95% ee.

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Recent Advances On Direct Formylation Reactions

Cited by 6 publications

References 79 publications

Multi-Functionality of Methanol in Sustainable Catalysis: Beyond Methanol Economy

Multi-Functionality of Methanol in Sustainable Catalysis: Beyond Methanol Economy

Lewis Acid-Mediated Friedel–Crafts-Type Formylation of Alkenes with Dichloromethyl Methyl Ether in the Presence of Pyridines

Enantioselective Construction of Oxindoles Bearing a Quaternary Carbon via Ni−Al Bimetal‐Catalyzed Formyl C−H Alkylation

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