133055-17-1Relevant articles and documents
Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
Choudhary, Shivani,Hamann, Henry J.,Ramachandran, P. Veeraraghavan
supporting information, (2020/11/13)
Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
supporting information, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates
Zheng, Shuai,Primer, David N.,Molander, Gary A.
, p. 7957 - 7961 (2017/11/10)
A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent and further validation by experimental results.