3531-24-6Relevant articles and documents
Reaction of tetramethylammonium fluoride with trifluoromethyltrimethylsilane
Adams, Dave J.,Clark, James H.,Hansen, Liv B.,Sanders, Victoria C.,Tavener, Stewart J.
, p. 123 - 125 (1998)
Tetramethylammonium fluoride reacts with either triluoromethyltrimethylsilane or trimethylsilylacetonitrile in acetonitrile to form a pentacoordinate silicon species, which can act as a source of either fluoride or cyanomethyl carbanion, depending on substrate.
Formation of Tetrahydrothiophenes via a Thia-Paternò-Büchi-Initiated Domino Photochemical Reaction
Kassir, Ahmad F.,Guillot, Régis,Scherrmann, Marie-Christine,Boddaert, Thomas,Aitken, David J.
, p. 8522 - 8527 (2020/11/12)
We have established photochemical access to thietane or tetrahydrothiophene compounds from thiobenzophenone derivatives and acrylonitrile, wherein the product selectivity is controlled by a simple adjustment of the reagent concentration in solution. Small libraries of five-membered ring sulfur-containing compounds were prepared through a thia-Paternò-Büchi reaction, followed by a previously unknown regioselective photochemical ring enlargement reaction in a domino process or a stepwise fashion. A mechanism is proposed to rationalize this ring enlargement reaction via a carbene species provided from photoexcited thiocarbonyl compounds.
5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations
Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
supporting information, p. 9496 - 9500 (2019/06/27)
The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.