A Practical and General Base‐Catalyzed Carbonylation of Amines for the Synthesis of <i>N</i>‐Formamides

Li, Wanfang; Wu, Xiao‐Feng

doi:10.1002/chem.201502107

Cited by 43 publications

(21 citation statements)

References 59 publications

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“…In the presence of 10-40 mol % of KOH or K 2 CO 3 , a range of amines were successfully formylated and provided the corresponding N-formamides in good to excellent yields. 77 The reaction is believed to proceed via the intermediacy of methyl formate. KOH dissolves in heated MeOH to form potassium methoxide, which is trapped by CO to give methyl formate after protonation by MeOH.…”

Section: Heteroatom-anion-mediated Carbonylationmentioning

confidence: 99%

The Chemistry of CO: Carbonylation

Peng

Geng

2019

Chem

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424

170

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Carbon monoxide is one of the most important C1 molecules in organic chemistry. Many novel procedures for its conversion have been developed, and some have even been industrialized. In this review, we discuss and categorize CO chemistry into four classes: (1) transition-metal-mediated carbonylation, (2) strong-acid-initiated cationic carbonylation, (3) anionic carbonylation, and (4) free-radical carbonylation. Relevant achievements are selected and discussed in detail.

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Section: Heteroatom-anion-mediated Carbonylationmentioning

confidence: 99%

The Chemistry of CO: Carbonylation

Peng

Geng

2019

Chem

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424

170

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“…Apart from nano Au-catalysis, the synthesis of formamides is feasible in the literature based on the catalytic transamidation of amines with HCONH 2 [ 38 ], treatment of amines with CO 2 and a hydrosilane or with H 2 under various catalytic conditions [ 39 , 40 , 41 ], Ru-catalyzed dehydrogenative coupling between amines [ 42 ] or nitriles [ 43 ] and methanol, and the base-catalyzed carbonylation of amines with carbon monoxide [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Formate Esters and Formamides Using an Au/TiO2-Catalyzed Aerobic Oxidative Coupling of Paraformaldehyde

2017

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A simple method for the synthesis of formate esters and formamides is presented based on the Au/TiO2-catalyzed aerobic oxidative coupling between alcohols or amines and formaldehyde. The suitable form of formaldehyde is paraformaldehyde, as cyclic trimeric 1,3,5-trioxane is inactive. The reaction proceeds via the formation of an intermediate hemiacetal or hemiaminal, respectively, followed by the Au nanoparticle-catalyzed aerobic oxidation of the intermediate. Typically, the oxidative coupling between formaldehyde (2 equiv) and amines occurs quantitatively at room temperature within 4 h, and there is no need to add a base as in analogous coupling reactions. The oxidative coupling between formaldehyde (typically 3 equiv) and alcohols is unprecedented and occurs more slowly, yet in good to excellent yields and selectivity. Minor side-products (2–12%) from the acetalization of formaldehyde by the alcohol are also formed. The catalyst is recyclable and can be reused after a simple filtration in five consecutive runs with a small loss of activity.

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“…Beside the use of formic acid and its derivatives as amine formylating reagents, recent developments focused on the use of sub‐stoichiometric amounts of a catalyst and a simpler formyl donor, such as methanol,– carbon monoxide– and CO 2 –. However, these methodologies are significantly restricted to the use of expensive transition metals and high pressure of toxic gases.…”

Section: Figurementioning

confidence: 99%

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

Dine

Evans

Rouden

et al. 2016

Chemistry A European J

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A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Brønsted acidity of acetic acid.

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A Practical and General Base‐Catalyzed Carbonylation of Amines for the Synthesis of N‐Formamides

Cited by 43 publications

References 59 publications

The Chemistry of CO: Carbonylation

The Chemistry of CO: Carbonylation

Synthesis of Formate Esters and Formamides Using an Au/TiO2-Catalyzed Aerobic Oxidative Coupling of Paraformaldehyde

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

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