145224-15-3Relevant academic research and scientific papers
Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters
Leng, Lingying,Ready, Joseph M.
, p. 13714 - 13720 (2021/11/16)
Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.
Pd-Catalysed Decarbonylation Free Approach to Carbonylative Esterification of 5-HMF to Its Aryl Esters Synthesis Using Aryl Halides and Oxalic Acid as C1 Source
Singh Chauhan, Arvind,Kumar, Ajay,Kumar Sharma, Ajay,Das, Pralay
supporting information, p. 12971 - 12975 (2021/08/06)
A decarbonylation free, polystyrene-supported, Pd (Pd@PS)-catalysed carbonylative esterification of the hydroxy group of 5-hydroxymethyl furfural (5-HMF) to its corresponding aryl esters has been developed. The use of Pd@PS, oxalic acid as CO source, and aryl halides was first explored for the aryl ester of 5-HMF synthesis. Here, we investigated the vital role of a polystyrene support to avoid the commonly known decarbonylation of 5-HMF. The reaction exhibits vast substrate scope with comparably good yield and catalyst recyclability.
Nickel-catalyzed selective conversion of two different aldehydes to cross-coupled esters
Hoshimoto, Yoichi,Ohashi, Masato,Ogoshi, Sensuke
supporting information; experimental part, p. 4668 - 4671 (2011/05/16)
In the presence of a Ni(0)/NHC catalyst, an equimolar mixture of aliphatic and aryl aldehydes can be employed to selectively yield a single cross-coupled ester. This reaction can be applied to a variety of aliphatic (1°, 2°, cyc-2°, and 3°) and aryl aldehyde combinations. The reaction represents 100% atom efficiency and generates no waste. Mechanistic studies have revealed that the striking feature of the reaction is the simultaneous coordination of two aldehydes to Ni(0).
Benzylic C-H activation and C-O bond formation via aryl to benzylic 1,4-palladium migrations
Kesharwani, Tanay,Larock, Richard C.
, p. 6090 - 6102 (2008/09/21)
A procedure for benzylic C-H activation has been developed using a palladium 1,4-aryl to benzylic migration as a key step. Carboxylates and phenoxides readily trap the resulting benzylic palladium intermediates obtained from palladium 'through space' migration. Aryl bromides and iodides have been successfully employed in this reaction, furnishing moderate to good yields. The mechanism of this reaction has been studied by deuterium-labeling experiments, which suggest that the migration of palladium from an aryl to a benzylic position occurs reversibly. The reaction conditions developed for the migration process also oxidize the neighboring benzylic alcohols to the corresponding aldehydes and ketones.
