22509-78-0Relevant articles and documents
Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation-Cyclization of Allylphenols
Triandafillidi, Ierasia,Sideri, Ioanna K.,Tzaras, Dimitrios Ioannis,Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 4254 - 4260 (2017/09/12)
A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o -allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H 2 O 2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o -allylphenols were cyclized in high yields..
Development of a 4,4′-biphenyl/phosphine-based COF for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene
Hausoul, Peter J. C.,Eggenhuisen, Tamara M.,Nand, Deepak,Baldus, Marc,Weckhuysen, Bert M.,Klein Gebbink, Robertus J. M.,Bruijnincx, Pieter C. A.
, p. 2571 - 2579 (2013/09/24)
The improved synthesis, characterisation and application of a microporous 4,4′-biphenyl/phosphine-based covalent organic framework (COF) for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene with phenol and glycerol are presented. The solid polyphosphine is amorphous, microporous and an excellent support for Pd(acac)2. Solid-state NMR and DRIFT analysis of materials of varying Pd-loading show that bis-phosphine complexes of palladium are preferably formed. Under solvent- and base-free conditions, high conversions and selectivities are obtained for this catalyst material with both phenol and glycerol as substrates. The product selectivity, with both butenylation and telomerisation activity observed with phenol, can be tuned by variation of the metal loading. For glycerol it is shown that the selectivity to the undesired tri telomer is low under all applied conditions and, remarkably, that the heterogeneous catalyst outperforms its homogeneous PPh 3-based counterpart.
Ruthenium-catalyzed o-allylation of phenols from allylic chlorides via cationic [Cp*(η3-allyl)(MeCN)RuX][PF6] complexes
Mbaye, Mbaye D.,Demerseman, Bernard,Renaud, Jean-Luc,Toupet, Loic,Bruneau, Christian
, p. 835 - 841 (2007/10/03)
The [Cp*(MeCN)3Ru(II)][PF6] complex is an efficient catalyst precursor for the O-allylation of phenols with allylic chlorides in the presence of K2CO3 under mild conditions. This ruthenium precursor affords branched allyl aryl ethers according to a regioselective reaction, which contrasts with the uncatalyzed nucleophilic substitution from the same substrates. Stable (η3-allyl)Ru(IV) cationic complexes resulting from the reaction of [Cp*(MeCN) 3Ru][PF6] with allylic halides were identified as intermediate catalytic species. An X-ray structure determination of the complex [Cp*(MeCHCHCH2)(MeCN)RuBr] [PF6] disclosed an (endo-trans-MeCHCHCH2) allylic ligand. The structural information obtained from the study of Cp*(allyl)Ru(IV) complexes indicated that electronic effects at the coordinated allylic ligand likely account for the better regioselectivity obtained from cinnamyl chloride as compared to aliphatic allylic chlorides.
