1517-82-4Relevant articles and documents
Stereochemistry of organic sulfur compounds: More than 100?years of history, current state and further challenges
Drabowicz, Józef
, p. 145 - 148 (2017)
In the paper presented are the author's subjective views on the most important achievements in the stereochemistry of organic sulfur compounds, which, as an object of research, has more than 100-year history. Prospects for further development are also men
Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid
Gafur, Sayed Habibul,Waggoner, Stephanie L.,Jacobsen, Eric,Hamaker, Christopher G.,Hitchcock, Shawn R.
, p. 4855 - 4866 (2018)
Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.
Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
, p. 1846 - 1855 (2019/02/14)
Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.
Palladium-Catalyzed Enantioselective C?H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
Zhu, Yu-Chao,Li, Yan,Zhang, Bo-Chao,Zhang, Feng-Xu,Yang, Yi-Nuo,Wang, Xi-Sheng
supporting information, p. 5129 - 5133 (2018/03/27)
The first example of PdII-catalyzed enantioselective C?H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) throu