Tetramethyl Orthosilicate (TMOS) as a Reagent for Direct Amidation of Carboxylic Acids

Braddock, D. Christopher; Lickiss, Paul D.; Rowley, Ben; Pugh, David; Purnomo, Teresa; Santhakumar, Gajan; Fussell, Steven J.

doi:10.1021/acs.orglett.7b03841

Cited by 73 publications

(47 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1A) our reaction design (Fig. 1B) is based upon the dual reactivity of hydrosilanes, which mediate direct amide coupling [23][24][25][26] and amide reduction in the presence of a metal catalyst. [27][28][29][30] Combining these processes gives a reductive amination reaction in which carbon-nitrogen bond formation is complete before reduction begins, thereby avoiding unwanted reduction of the carboxylic acid, leading to alcohol by-products.…”

Section: Resultsmentioning

confidence: 99%

A practical catalytic reductive amination of carboxylic acids

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

A practical catalytic reductive amination of carboxylic acids

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Directly between carboxylic acids and amines and would not require the isolation of intermediates; • Catalytic and atom efficient (e.g., no coupling reagents); • Waste free (e.g., no solvents and minimal purification); and • Fast (no extended reaction times) [17,18].…”

mentioning

confidence: 99%

Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids

2020

View full text Add to dashboard Cite

Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.

show abstract

“…Several coumarin amide derivatives are shown to be pesticidal, 34 anti-bacterial, 35 cytotoxic, 36 chemosensors, 37 and hMAO inhibitors. 38 In recent years, several methods were reported for the synthesis of amines from the corresponding carboxylic acids and amines catalysed by diborane, 39 tetramethyl orthosilicate, 40 aryl boronic acid, 41 and XtalFluor-E. 42 However, these methods involve expensive catalysts, volatile solvents and anhydrous inert conditions. Therefore, to synthesis amides from coumarins via a catalyst-free method, a one-pot domino decarboxylative amidation reaction was Scheme 2 Optimization of reaction conditions.…”

Section: Resultsmentioning

confidence: 99%