39627-14-0Relevant articles and documents
Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
supporting information, p. 2268 - 2273 (2019/04/10)
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
Copper-catalyzed alkene arylation with diaryliodonium salts
Phipps, Robert J.,McMurray, Lindsay,Ritter, Stefanie,Duong, Hung A.,Gaunt, Matthew J.
supporting information; experimental part, p. 10773 - 10776 (2012/08/07)
Alkenes and arenes represent two classes of feedstock compounds whose union has fundamental importance to synthetic organic chemistry. We report a new approach to alkene arylation using diaryliodonium salts and Cu catalysis. Using a range of simple alkenes, we have shown that the product outcomes differ significantly from those commonly obtained by the Heck reaction. We have used these insights to develop a number of new tandem and cascade reactions that transform readily available alkenes into complex arylated products that may have broad applications in chemical synthesis.
Nickel catalysed coupling of allylamines and boronic acid
Trost, Barry M.,Spagnol, Michel D.
, p. 2083 - 2096 (2007/10/02)
Allylamines function as substrates for cross-coupling with boronic acids in the presence of nickel(0) catalysts rather than palladium(0) catalysts.Aryl-, vinyl- and methyl-boronic acids function well.With vinyl derivatives, E-isomers couple more efficiently than Z-isomer and both fully retain the geometrical integrity.Methylations preferably employ the boronic esters like 2-methyl-1,3,2-benzodioxaborole or 2-methyl-1,3,2-dioxaborolane rather than methylboronic acid.The stereochemistry of the reaction involves a net inversion with respect to the allylamine.The regioselectivity is a function of ligand.Generally, sterically bulky donor phosphines promote new C-C bond formation at the less substituted position.Bidentate ligands, notably 1,1'-binaphthyl-2,2'-ylbis(diphenylphosphinite) (BINAPO), promote new C-C bond formation at the more substituted allyl terminus.The amines appear to be the preferred partner compared to allyl alcohols and esters with the boronic acids and give higher stereospecificity.
