40089-15-4Relevant academic research and scientific papers
A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides
Zheng, Bing,Jia, Tiezheng,Walsh, Patrick J.
supporting information, p. 165 - 178 (2014/03/21)
An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indolebased phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK a up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)2].
Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds
Duong, Hung A.,Gilligan, Ruth E.,Cooke, Michael L.,Phipps, Robert J.,Gaunt, Matthew J.
, p. 463 - 466 (2011/03/16)
Strong competition: A method for the meta-selective arylation of the highly versatile α-aryl carbonyl motif using diaryliodonium salts is described. In this CuII-catalyzed process the remote carbonyl group is capable of overpowering even strongly para-directing functionalities to form the elusive meta-products (see scheme). Remarkably, the arylation process can also operate under metal-free conditions.
Practical synthesis of amides from alkynyl bromides, amines, and water
Chen, Zheng-Wang,Jiang, Huan-Feng,Pan, Xiao-Yan,He, Zai-Jun
experimental part, p. 5920 - 5927 (2011/09/19)
A general and efficient method for the synthesis of a wide range of amides is described here. The reactions were conducted under convenient conditions and provided secondary and tertiary amides in moderate to excellent yields. A variety of amines and substituted alkynyl bromides were used to investigate the scope of the reactions.
