138172-31-3Relevant academic research and scientific papers
Br?nsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes
Cai, Xiao,Keshavarz, Amir,Omaque, Justin D.,Stokes, Benjamin J.
supporting information, p. 2626 - 2629 (2017/05/24)
Using triphenylmethylium tetrakis(pentafluorophenyl)borate as a convenient Br?nsted acid precatalyst, β-(α,α-dimethylbenzyl)styrenes are shown to cyclize efficiently to afford a variety of new indanes that possess a benzylic quaternary center. The geminal dimethyl-containing quaternary center is proposed to be necessary to arm the substrate for cyclization through steric biasing.
A new synthetic approach to biaryls of the rhazinilam type. Application to synthesis of three novel phenylpyridine-carbamate analogues
Bonneau, Anne-Laure,Robert, Nicolas,Hoarau, Christophe,Baudoin, Olivier,Marsais, Francis
, p. 175 - 183 (2008/03/28)
The synthesis of three novel racemic phenylpyridine-carbamate analogues of rhazinilam and their biological evaluation as inhibitors of microtubule assembly and disassembly by interaction with tubulin are described. The sterically hindered ortho-disubstituted biaryl unit as the challenging key structural element is first obtained by a sequential regiocontrolled nucleophilic addition of a lithium ortho-lithiohomobenzylic alkoxide species to 3-bromo-5-oxazolyl pyridine as the electrophile and a subsequent oxidation step. The incorporation of the amino group by replacement of the bromide has been achieved using a Buchwald-Hartwig amination coupling. Ultimate deprotection steps furnished free-amino and free-hydroxyl appendages which were connected by phosgenation to furnish the nine-membered median carbamate ring. This journal is The Royal Society of Chemistry.
The Palladium-Catalyzed C-H Activation of Benzylic gem-Dialkyl Groups
Baudoin, Olivier,Herrbach, Audrey,Gueritte, Francoise
, p. 5736 - 5740 (2007/10/03)
Palladacyclic intermediates effectively lower the high energy barrier to cleavage of a C(sp3)-H bond. C-H activation of benzylic gem-dialkyl groups of bromo- and iodobenzenes produces olefins and cyclobutabenzenes, respectively, without homocoupling (see scheme).
