22808-95-3Relevant academic research and scientific papers
Palladium-catalyzed esterification of aryl halides using aryl formates without the use of external carbon monoxide
Fujihara, Tetsuaki,Hosoki, Tomoya,Katafuchi, Yuko,Iwai, Tomohiro,Terao, Jun,Tsuji, Yasushi
, p. 8012 - 8014 (2012/09/08)
Aryl formates are efficient carbon monoxide sources in palladium-catalyzed esterification of aryl halides. The carbonylation readily proceeds at ambient pressure without the use of external carbon monoxide to afford the corresponding esters in high yields.
Influence of ortho substituents on 17O NMR chemical shifts in phenyl esters of substituted benzoic acids
Nummert, Vilve,Maeemets, Vahur,Piirsalu, Mare,Koppel, Ilmar A.
body text, p. 539 - 552 (2012/04/23)
17O NMR spectra for 29 phenyl esters of ortho-, para,- and meta-substituted benzoic acids, X-C6H4CO2C 6H5, at natural abundance in acetonitrile were recorded. The δ(17O) values o
Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids
Watson, Donald A.,Fan, Xuexiang,Buchwald, Stephen L.
supporting information; experimental part, p. 7096 - 7101 (2009/05/09)
(Chemical Equation Presented) A mild, functional group tolerant method of the preparation of phenyl esters from aryl chlorides via palladium-catalyzed carbonylation is described using atmospheric pressure of carbon monoxide. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions. Direct preparation of alkyl esters and carboxylic acids is also demonstrated, providing the first method for the preparation of methyl and ethyl esters from aryl chlorides without pressured reactors.
Nucleophilic displacement at the benzoyl centre: A study of the change in geometry at the carbonyl carbon atom
Colthurst, Matthew J.,Williams, Andrew
, p. 1493 - 1497 (2007/10/03)
The second-order rate constants for the reaction between hydroxide ion and phenoxide ion with 4-nitrophenyl esters of substituted benzoic acids in 10% acetonitrile-water (v/v) solution obey Hammett σ correlations. The values of the Hammett ρ of 1.67 (κArO) and 2.14 (κOH) are consistent with a large change in hybridization at the central carbon by comparison with the ρ value for a standard reaction where a full sp2 to sp3 change occurs. The transition state for the concerted reaction thus has a substantially tetrahedral geometry. The observation of the anti-Hammond effect whereby the ρ value for the hydroxide ion exceeds that of the less reactive phenoxide ion is consistent with a concerted, ANDN, mechanism for these reactions. A stepwise mechanism, AN + DN, is unlikely to yield a measurable break in the Hammett correlation for a change in the benzoyl substituent if the partitioning of the putative tetrahedral intermediate involves forward and reverse reactions with Hammett correlations possessing similar ρ values.
