63064-23-3Relevant academic research and scientific papers
Intermolecular 1,2-Difunctionalization of Alkenes Enabled by Fluoroamide-Directed Remote Benzyl C(sp3)-H Functionalization
Zhong, Long-Jin,Xiong, Zhi-Qiang,Ouyang, Xuan-Hui,Li, Yang,Song, Ren-Jie,Sun, Qing,Lu, Xin,Li, Jin-Heng
supporting information, p. 339 - 348 (2022/01/08)
A copper-catalyzed remote benzylic C-H functionalization strategy enabling 1,2-difunctionalization of alkenes with 2-methylbenzeneamides and nucleophiles, including alcohols, indoles, pyrroles, and the intrinsic amino groups, is reported, which is charact
Synthesis of Secondary Amides from Thiocarbamates
Mampuys, Pieter,Ruijter, Eelco,Orru, Romano V. A.,Maes, Bert U. W.
supporting information, p. 4235 - 4239 (2018/07/29)
The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation of challenging amides that are not or hardly accessible via classical approaches.
A Practical and General Amidation Method from Isocyanates Enabled by Flow Technology
Williams, Jason D.,Kerr, William J.,Leach, Stuart G.,Lindsay, David M.
supporting information, p. 12126 - 12130 (2018/09/11)
The addition of carbon nucleophiles to isocyanates represents a conceptually flexible and efficient approach to the preparation of amides. This general synthetic strategy has, however, been relatively underutilized owing to narrow substrate tolerance and the requirement for less favourable reaction conditions. Herein, we disclose a high-yielding, mass-efficient, and scalable method with appreciable functional group tolerance for the formation of amides by reaction of Grignard reagents with isocyanates. Through the application of flow chemistry and the use of substoichiometric amounts of CuBr2, this process has been developed to encompass a broad range of substrates, including reactants found to be incompatible with previously published procedures.
Facile synthesis of sterically hindered and electron-deficient secondary amides from isocyanates
Sch?fer, Gabriel,Matthey, Coraline,Bode, Jeffrey W.
supporting information, p. 9173 - 9175 (2012/11/07)
The big easy: The direct coupling of Grignard reagents to isocyanates provides a facile and robust solution for the synthesis of sterically hindered and electron-deficient secondary amides. The products are obtained in high yields without the need for excess reagents or chromatographic purification. Copyright
