1400191-40-3Relevant academic research and scientific papers
Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
Cao, Rui,Li, Jing-Sheng,Song, Geyang,Tang, Wei-Jun,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
supporting information, p. 21536 - 21542 (2021/08/23)
The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.
Consecutive intermolecular reductive hydroamination: Cooperative transition-metal and chiral Br?nsted acid catalysis
Fleischer, Steffen,Werkmeister, Svenja,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias
supporting information; experimental part, p. 9005 - 9010 (2012/09/25)
Enantiomerically pure chiral amines are of increasing importance and commercial value in the fine chemical, pharmaceutical, and agrochemical industries. Here, we describe the straightforward synthesis of chiral amines by combining the atom-economic and environmentally friendly hydroamination of alkynes with an enantioselective hydrogenation of in situ generated imines by using inexpensive hydrogen. By following this novel approach, a wide range of terminal alkynes can be reductively hydroaminated with primary amines including alkyl-, and arylalkynes as well as aryl and heteroaryl amines. Excellent yields and selectivities up to 94 % ee and 96 % isolated yield were obtained.
