10276-85-4Relevant articles and documents
Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments
Pongpamorn, Pornkanok,Kiattisewee, Cholpisit,Kittipanukul, Narongyot,Jaroensuk, Juthamas,Trisrivirat, Duangthip,Maenpuen, Somchart,Chaiyen, Pimchai
, p. 5749 - 5753 (2021)
Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.
-
Eliel,Anderson
, p. 547 (1952)
-
Hydro-dediazoniation of diazonium salts using trichlorosilane: New cleavage conditions for the T1 traceless linker
Lormann, Matthias,Dahmen, Stefan,Br?se, Stefan
, p. 3813 - 3816 (2000)
An efficient, selective cleavage of triazenes and in situ hydro- dediazoniation of the intermediately formed diazonium salts with trichlorosilane (HSiCl3) in liquid as well on solid phase is reported. Starting from anilines, attachment to solid support and subsequent cleavage gives rise to the corresponding unsubstituted arenes. This cleavage reagent is compatible with various functionalities (esters, amides, nitro groups, halides, aliphatic double and triple bonds). (C) 2000 Elsevier Science Ltd.
Esterification by microwave irradiation on activated carbon
Fan, Xingjun,Yuan, Keguo,Hao, Caili,Li, Nan,Tan, Ganzu,Yu, Xianda
, p. 287 - 290 (2000)
-
Improved ester interchange catalysts
Kissling, Rebecca M.,Gagne, Michel R.
, p. 4209 - 4212 (2000)
(equation presented) Mixed alkoxide/aryloxide clusters are long-lived and milder than previously reported ester interchange catalysts. They completely transform difficult substrates in a single synthetic operation with lower catalyst and reagent ester loadings. In addition to superior activities, these mixed clusters are kinetically less basic toward enolizable esters.
Redox-active alkylsulfones as precursors for alkyl radicals under photoredox catalysis
Patel, Sandeep,Paul, Biprajit,Paul, Hrishikesh,Shankhdhar, Rajat,Chatterjee, Indranil
, p. 4857 - 4860 (2022/04/19)
A method for generating alkyl radicals using visible-light photoredox catalysis is described. This procedure was found to present an efficient means to access a diverse collection of 1°, 2°, and 3° alkyl radicals through the single-electron transfer of sulfones under mild reaction conditions. These alkyl radicals generated via the reductive desulfonylation of readily synthesized and stable alkylsulfones were engaged to forge C-C bonds. A detailed study was also carried out to shed light on the mechanism.
N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading
Berkessel, Albrecht,Biswas, Animesh,Harnying, Wacharee,Sudkaow, Panyapon
supporting information, p. 19631 - 19636 (2021/08/09)
We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.
