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5‐(Cyano)dibenzothiophenium Triflate: A Sulfur‐Based Reagent for Electrophilic Cyanation and Cyanocyclizations
Author(s) -
Li Xiangdong,
Golz Christopher,
Alcarazo Manuel
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904557
Subject(s) - cyanation , electrophile , chemistry , reagent , trifluoromethanesulfonate , enol , combinatorial chemistry , silylation , reactivity (psychology) , thiophene , lewis acids and bases , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract The synthesis of 5‐(cyano)dibenzothiophenium triflate 9 , prepared by activation of dibenzo[b,d]thiophene‐5‐oxide with Tf 2 O 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.