371256-71-2Relevant academic research and scientific papers
Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins
Labrosse,Lhoste,Sinou
, p. 6634 - 6642 (2001)
Palladium-catalyzed condensation of benzene-1,2-diol with various propargylic carbonates, afforded regio- and stereoselectively 2,3-dihydro-2-ylidene-1,4-benzodioxins. The reaction is suggested to proceed by the formation of a (σ-allenyl)palladium complex, followed by the intermolecular attack of the phenoxide ion on this complex to generate a new (σ-allyl)palladium complex in equilibrium with the corresponding (η3-allyl)palladium complex. Intramolecular attack of the phenoxide ion afforded the corresponding benzodioxan compound. This last attack occurs predominantly at the more electrophilic end of the (η3-allyl)palladium intermediate. The Z- or E-stereochemistry of the products was established by 1H NMR and proton NOE measurements and also by X-ray analysis on an example. The Z-stereochemistry generally observed is in agreement with the formation of this (η3-allyl)palladium intermediate. However, in the case of tertiary propargylic carbonates, the E-stereochemistry generally observed could be explained by an intramolecular attack of the phenoxide ion on the intermediate (σ-allyl)palladium complex, in slow equilibrium with the (η3allyl)palladium complex.
Tandem Benzylic Oxidation/Dihydroxylation of α-Vinyl- and α-Alkenylbenzyl Alcohols
Fernandes, Rodney A.,Kattanguru, Pullaiah
, p. 92 - 107 (2015/10/19)
A de novo tandem benzylic oxidative dihydroxylation of α-vinyl- and α-alkenylbenzyl alcohols has been developed to give α,β-dihydroxypropiophenones (=2,3-dihydroxy-1-phenylpropan-1-ones) and α,β-dihydroxyalkyl phenones. This method was shown to be substrate-selective and specific for the oxidation of benzylic alcohols.
PMA-silica gel catalyzed propargylation of aromatic compounds with arylpropargyl alcohols under solvent-free conditions
Srihari, Pabbaraja,Reddy, Joolakanti Shyam Sunder,Mandal, Satadru Sekhar,Satyanarayana, Kamani,Yadav, Jhillu Singh
body text, p. 1853 - 1860 (2009/04/04)
PMA-silica gel has been utilized to catalyze efficiently the propargylation of aromatic compounds with arylpropargyl alcohols in the absence of solvent under environmentally benign conditions.
