103475-54-3Relevant academic research and scientific papers
Synthesis of alkylbenzenes by Friedl-Crafts reactions catalysed by K10-montmorillonite
Sieskind,Albrecht
, p. 1197 - 1200 (1993)
Monoalkylation of benzene with primary, secondary and tertiary alcohols took place in high yields when K10-montmorillonite was used as acidic catalyst. Unexpected formation of 1-phenylalkylbenzenes occurred, beside other isomers with primary alcohols. Mon
Teaching an old carbocation new tricks: Intermolecular C-H insertion reactions of vinyl cations
Popov, Stasik,Shao, Brian,Bagdasarian, Alex L.,Benton, Tyler R.,Zou, Luyi,Yang, Zhongyue,Houk,Nelson, Hosea M.
, p. 381 - 387 (2018/08/07)
Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium-weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond-forming reactions, including carbon-hydrogen (C-H) insertion into unactivated sp3 C-H bonds and reductive Friedel-Crafts reactions with arenes. Moreover, we conducted computational studies of these alkane C-H functionalization reactions and discovered that they proceed through nonclassical, ambimodal transition structures. This reaction manifold provides a framework for the catalytic functionalization of hydrocarbons using simple ketone derivatives.
