74738-56-0Relevant articles and documents
Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst
Chen, Jianxia,Namila,Bai, Chaolumen,Baiyin, Menghe,Agula, Bao,Bao, Yong-Sheng
, p. 25168 - 25176 (2018/07/29)
Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, which are widely used in the synthetic and pharmaceutical industry.
Kinetic study on nucleophilic displacement reactions of y-substituted-phenyl 2-methylbenzoates with cyclic secondary amines in acetonitrile: Effects of modification of 2-meo in benzoyl moiety by 2-me on reactivity and reaction mechanism
Lee, Ji-Youn,Kim, Mi-Yeon,Um, Ik-Hwan
, p. 3795 - 3799 (2014/01/17)
The second-order rate constants (kN) have been measured spectrophotometrically for nucleophilic substitution reactions of Y-substituted-phenyl 2-methylbenzoates (6a-e) with a series of cyclic secondary amines in MeCN at 25.0 ± 0.1 oC. Comparison of the kN values for the reactions of 4-nitrophenyl 2-methylbenzoate (6d) with those reported previously for the corresponding reactions of 4-nitrophenyl 2-methoxybenzoate (5) reveals that 6d is significantly less reactive than 5, indicating that modification of 2-MeO in the benzoyl moiety of 5 by 2-Me (i.e., 5 ? 6d) causes a significant decrease in reactivity. This supports our previous report that aminolysis of 5 proceeds through a six-membered cyclic intermediate, which is highly stabilized through intramolecular H-bonding interactions. The Bronsted-type plot for the reactions of 6d with a series of cyclic secondary amines is linear with ssnuc = 0.71, which appears to be a lower limit of ssnuc for a stepwise mechanism with breakdown of an intermediate (T±) being rate-determining step (RDS). The Bronsted-type plot for the reactions of 6a-e with piperidine is curved, i.e., the slope of Bronsted-type plot (sslg) decreases from -1.05 to -0.41 as the leavinggroup basicity decreases. The nonlinear Bronsted-type plot has been taken as evidence for a stepwise mechanism with a change in RDS (e.g., from the k2 step to the k1 process as the leaving-group basicity decreases). Dissection of kN into the microscopic rate constants associated with the reactions of 6a-e with piperidine (e.g.,k1 and k2/k-1 ratio) also supports the proposed mechanism.
Palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols
Luo, Fang,Pan, Changduo,Cheng, Jiang,Chen, Fan
supporting information; experimental part, p. 5878 - 5882 (2011/09/12)
A palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols to access aryl benzoate derivatives is described. The procedure tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, fluoro and bromo groups. Thus, it represents a practically alternative method to access aryl benzoate derivatives.
