599-86-0Relevant articles and documents
Visible Light-Driven Synthesis of Amine–Sulfonate Salt Derivatives: A Step towards Green Approach
Kamal, Arsala,Kumari, Savita,Kushwaha, Ambuj Kumar,Maury, Suresh Kumar,Singh, Himanshu Kumar,Singh, Sundaram,Srivastava, Vandana
, (2022/02/17)
In this work, a novel strategy for the straightforward visible-light-driven synthesis of biologically active, industrially important, and stable amine–sulfonate salts have been reported from p-Toluenesulfonic acid and amines, which provide extremely high yield without side product formation. The reaction was performed without catalyst under visible light irradiation and had an excellent functional group tolerance. The structure of the prepared compounds were confirmed through 1H NMR, 13C NMR, and Mass spectroscopic studies, and similarly, the molecular structure of compound 3b was established through single-crystal XRD-analysis. The advantages of this method meet the requirements of sustainable and green synthetic chemistry, and it provides a direct way to create valuable amine-sulfonate salt.
Ligand-Regulated Palladium-Catalyzed Regiodivergent Hydroarylation of the Distal Double Bond of Allenamides with Aryl Boronic Acid
Dong, Yunhui,Du, Xin,Li, Xinling,Liu, Hui,Liu, Qing,Wang, Ping,Zhang, Daopeng,Zhang, Lizhi,Zhao, Huan
, p. 13276 - 13288 (2021/10/12)
The ligand-regulated regiodivergent hydroarylation of the distal double bond of allenamides with aryl boronic acid was achieved in the presence of palladium(II) catalysts, delivering a variety of functionalized enamide with excellent E selectivity and Markovnikov/anti-Markovnikov selectivity. Two possible coordination intermediates were proposed to be responsible for the regiodivergent hydroarylation: (1) The coordination Intermediate I, which was proposed to be formed through the coordination of MeCN, distal double bond, phenyl to palladium, led to the aryl group away from the Intermediate I, inducing excellent E selectivity and anti-Markovnikov selectivity. (2) A switch of regioselectivity to 1,2-Markovnikov hydroarylation was obtained using bidentate phosphine ligand (dppf or Xantphos). The formed coordination Intermediate II led to the N-tether away from the Intermediate II and at the trans position of aryl, resulting in excellent E selectivity and Markovnikov selectivity. Meanwhile, tentative investigation on the mechanism proved that the hydron source of this hydroarylation is more likely to be boronic acid. The transmetallation between aryl boronic acid and palladium catalyst was the initial step of this transformation.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.