95932-41-5Relevant academic research and scientific papers
Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
K?nig, Burkhard,Wang, Hua,Wang, Shun
, p. 1653 - 1665 (2021)
Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.
Catalytic Strategy for Regioselective Arylethylamine Synthesis
Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.
, p. 4147 - 4153 (2019/03/07)
A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.
Phase transfer catalysis in the tert-butyloxycarbonylation of alcohols, phenols, enols, and thiols with di-tert-butyl dicarbonate
Houlihan, F.,Bouchard, J.,Frechet, J. M. J.,Willson, C. G.
, p. 153 - 162 (2007/10/02)
It is shown that the tert-butyloxycarbonylation of phenols, alcohols, enols, and thiols can be accomplished by reaction of these functionalities with di-tert-butyl bicarbonate under phase transfer conditions.The reactions proceed in high yield and can also be used for the introduction of t-BOC groups onto functionalized polymer backbones such as poly(p-hydroxystyrene).In addition, a study is made of the selectivity towards tert-butyloxycarbonilation of various polyfunctional compounds.
