41796-41-2Relevant academic research and scientific papers
Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion
Ananikov, Valentine P.,Burykina, Julia V.,Gordeev, Evgeniy G.,K?nig, Burkhard,Shlapakov, Nikita S.
, p. 10061 - 10070 (2020/10/13)
An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products-four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. This journal is
Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones
Ishitobi, Kota,Muto, Kei,Yamaguchi, Junichiro
, p. 11685 - 11690 (2019/12/02)
A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.
Nickel-Catalyzed Regioselective Cleavage of Csp2-S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes
Chen, Jinyang,Chen, Sihai,Xu, Xinhua,Tang, Zhi,Au, Chak-Tong,Qiu, Renhua
, p. 3246 - 3255 (2016/05/19)
We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H2O2 as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.
PREPARATION OF ALKENYL SULFIDES AND ENAMINES BY ALKYLIDENATION OF CARBOXYLIC ACID DERIVATIVES
Takai, Kazuhiko,Fujimura, Osamu,Kataoka, Yasutaka,Utimoto, Kiitiro
, p. 211 - 214 (2007/10/02)
Treatment of S-alkyl thioesters with a reagent prepared from RCHBr2, Zn, TiCl4, and TMEDA in THF at 25 degC gives Z-alkenyl sulfides selectively in good to excellent yields.Using the alkylidenation method, ketene dithioacetals and enamines are produced fr
