1950-77-2Relevant academic research and scientific papers
Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, (2021/10/26)
A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
Copper-Catalyzed Difunctionalization of Allenes with Sulfonyl Iodides Leading to (E)-α-Iodomethyl Vinylsulfones
Lu, Ning,Zhang, Zhiguo,Ma, Nana,Wu, Conghui,Zhang, Guisheng,Liu, Qingfeng,Liu, Tongxin
supporting information, p. 4318 - 4322 (2018/07/29)
A highly regioselective iodosulfonylation of allenes in the presence of CuI and 1,10-phenanthroline has been developed for the synthesis of various useful (E)-α-iodomethyl vinylsulfones in moderate to excellent yields. This practical reaction is fast, operationally simple, and in particular, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity. The selectivity was illustrated by a conceptual DFT analysis.
Catalyst-controlled selectivity in C-S bond formation: Highly efficient synthesis of C2- and C3-sulfonylindoles
Yang, Yong,Li, Wanmei,Xia, Chengcai,Ying, Beibei,Shen, Chao,Zhang, Pengfei
, p. 304 - 307 (2016/02/05)
Exploring a potential catalyst system for catalyst-controlled selectivity in C-S bond formation is a fascinating challenge. Herein, we described two novel and highly efficient methods for the selective synthesis of C2- and C3-sulfonylindoles showing good biological activities by employing iodide and copper catalysts, respectively. Mechanistic studies point to the crucial role of the electronic properties of the sulfonylated intermediates. I see two and I see three: Two novel and highly efficient methods for the selective synthesis of C2- and C3-sulfonylindoles by employing iodide and copper catalysts, respectively, are described. Mechanistic studies point to the crucial role of the electronic properties of the sulfonylated intermediates. phen=1,10-phenantroline, TBHP=tert-butyl hydroperoxide.
Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
, p. 3125 - 3131 (2014/06/10)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
Generation and alkylation of 2-boryl allylic sulfone anions
Altenhofer, Erich F.,Harmata, Michael
supporting information, p. 2365 - 2367 (2013/06/27)
The deprotonation and electrophilic trapping of an allylic sulfone substituted at the 2 position by a pinacol boronate results in the formation of the corresponding alkylation products. The ability of the boronate ester to tolerate the sulfonyl carbanion suggests a broader application of the methodology to prepare a wide range of functionalized boronates. The Royal Society of Chemistry.
ORGANIC SYNTHESIS WITH SULPHONES - XVII. THE ANTI-MARKOWNIKOFF HALOSULPHONYLATION OF OLEFINS VIA AN IONIC PATHWAY, AND A NEW METHOD OF PREPARING BENZENESULPHONYL IODIDE
Harwood, L. M.,Julia, M.,Thuillier, G. Le
, p. 2483 - 2487 (2007/10/02)
Iodine and bromine in the presence of sodium benzenesulphinate react with olefins in acetone solution to give halosulphones resulting from an apparent steric direction of attack at the intermediate halonium ion.A straightforward preparation of benzenesulphonyl iodide from benzenesulphonyl chloride and sodium iodide is also described.
