23261-40-7Relevant 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.
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
