37619-13-9Relevant academic research and scientific papers
Palladium-catalyzed intermolecular coupling of aryl halides and amides
Yin, Jingjun,Buchwald, Stephen L.
, p. 1101 - 1104 (2000)
The first general intermolecular C-N bond-forming reactions between aryl halides and amides were realized using a palladium catalyst with Xantphos as the ligand. Aryl triflates, carbamates, and sulfonamides are also viable substrates for the amidations, which proceed at 45-110 °C with 1-4 mol% of Pd catalyst in 66-99% yields and exhibit good functional group compatibility.
Acceleration of Pd-Catalyzed Amide N-Arylations Using Cocatalytic Metal Triflates: Substrate Scope and Mechanistic Study
Becica, Joseph,Dobereiner, Graham E.
, p. 5862 - 5870 (2017/09/15)
The Pd/xantphos-catalyzed cross-coupling of amides and aryl halides is accelerated by cocatalytic metal triflate additives. A survey of nitrogen nucleophiles reveals improved yields for a variety of N-aryl amide products when Al(OTf)3 is employed as a catalytic additive, with some exceptions. Initial rates of catalysis indicate that the Lewis acid acceleration is more pronounced when bromobenzene (PhBr) is used in comparison with iodobenzene (PhI). The observation of an aryl halide dependence on rate and various qualitative kinetic experiments are consistent with a mechanism in which ligand exchange of halide for amide ("transmetalation") is turnover limiting. The mechanism may be different depending on whether PhBr or PhI is used as a coupling partner. Oxidative addition complexes (xantphos)Pd(Ph)(X) (X = Br, I; xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene), likely intermediates in catalysis, have been prepared; their differing interactions with Yb(OTf)3 in solution resemble the halide dependence of the catalytic mechanism, which we propose originates from a reversible Lewis acid mediated halide abstraction during catalysis.
The copper-catalyzed aerobic oxidative amidation of tertiary amines
Cheng, Hui-Cheng,Hou, Wen-Jun,Li, Zeng-Wen,Liu, Ming-Yu,Guan, Bing-Tao
supporting information, p. 17596 - 17599 (2015/12/08)
A general and efficient method for the synthesis of tertiary amides has been developed via the copper-catalyzed aerobic oxidative amidation of tertiary amines. Due to the use of the O2 oxidant, various functional groups were well tolerated under the present conditions. Extensive substrates studies demonstrated its potential as a practical approach for the synthesis of tertiary amides.
