7515-28-8Relevant academic research and scientific papers
Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenylmethane
Nikolic,Uscumlic,Juranic
, p. 664 - 671 (2007)
The rate constants for the reaction of 2-methyl-cyclohex-1-enylcarboxylic, 2-phenylcyclohex-1-enylcarboxylic, and 2-methylbenzoic and 2-phenylbenzoic acids with diazodiphenyl-methane were determined in 14 various solvents at 30°C. To explain the kinetic results through solvent effects, the second-order rate constants of the examined acids were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The quantitative relationship between the molecular structure and the chemical reactivity has been discussed, as well as the effect of geometry on the reactivity of the examined molecules. The geometric data of all the examined compounds corresponding to the energy minima in solvent, simulated as dielectric continuum, obtained using semiempirical MNDO-PM3 energy calculations.
Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids
Empel, Claire,Nguyen, Thanh Vinh,Koenigs, Rene M.
supporting information, p. 548 - 553 (2021/01/26)
Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
An efficient metal-free oxidative esterification and amination of benzyl C-H bond
Liu, Saiwen,Chen, Ru,He, Guowen,Zhang, Jin
, (2020/04/09)
An esterification and amination of benzylic C-H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidati
Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources
Lai, Ming,Qi, Xinxin,Wu, Xiao-Feng
, p. 3776 - 3778 (2019/06/24)
An efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources and also reaction partners. A wide range of benzyl benzoates was obtained in good to excellent yields.
Iron(III)-catalyzed direct synthesis of diphenylmethyl esters from 2-diphenylmethoxypyridine
Tran, Van Hieu,La, Minh Thanh,Kim, Hee-Kwon
, p. 2379 - 2387 (2019/07/03)
A highly efficient method has been developed for the synthesis of diphenylmethyl (DPM) esters from 2-diphenylmethoxypyridine. Various carboxylic acids readily reacted with 2-diphenylmethoxypyridine in the presence of FeCl3 as a catalyst to provide the desired DPM esters with high yields. The procedure is facile and enables effective synthesis of a variety of esters for the protection of carboxylic acids.
Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
Mahajani, Nivedita S.,Meador, Rowan I. L.,Smith, Tomas J.,Canarelli, Sarah E.,Adhikari, Arijit A.,Shah, Jigisha P.,Russo, Christopher M.,Wallach, Daniel R.,Howard, Kyle T.,Millimaci, Alexandra M.,Chisholm, John D.
, p. 7871 - 7882 (2019/06/27)
Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.
Photocatalytic oxidation synthesis method of diphenylmethanol ester
-
Paragraph 0021; 0042; 0043, (2019/03/08)
The invention discloses a photocatalytic oxidation synthesis method of diphenylmethanol ester. The method is characterized in that diphenylmethanol and carboxylic acid are used as reaction substrates,2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and ter
Metal-Free Aerobic Oxidative C–O Coupling of C(sp3)–H with Carboxylic Acids Catalyzed by DDQ and tert-Butyl Nitrite
Pan, Decheng,Pan, Zilong,Hu, Zhiming,Li, Meichao,Hu, Xinquan,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu
, p. 5650 - 5655 (2019/08/20)
The formation of the C–O bond is one of the hot topics in the area of C(sp3)–H bond functionalization. A metal-free oxidative cross-coupling between benzylic C(sp3)–H bond and carboxylic acids has been developed. The reactions were performed with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the catalyst, tert-butyl nitrite (TBN) as the co-catalyst, and molecular oxygen as the terminal oxidant. A variety of diarylmethanes could be successfully coupled with various carboxylic acids to obtain diarylmethanol esters in good to excellent yields. In addition, 2-benzylbenzoic acids could be converted into phthalides in moderate yields through an intramolecular oxidative cyclization.
Preparation method for synthesizing ester compound by using N-Boc amide as raw material
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Paragraph 0042; 0043, (2019/03/28)
The invention relates to a preparation method for synthesizing an ester compound by using N-Boc amide as a raw material. According to the method, an inorganic base is used as a catalyst; the N-Boc amide is subjected to an intermolecular nucleophilic substitution reaction with various alcohol compounds; and various ester compounds can be efficiently obtained. The method has the advantages of beingmild in reaction condition, simple and convenient to operate, high in yield and favorable in functional-group compatibility.
