60045-26-3Relevant articles and documents
Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process
Guo, Lin,Xia, Raymond Yang,Xia, Wujiong,Yang, Chao,Zhang, Haoxiang,Zhou, Xiao
supporting information, (2022/03/31)
A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety of ketones as major products. The reaction proceeds at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibits several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). (Figure presented.).
Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights
Mai, Binh Khanh,Koenigs, Rene M.,Nguyen, Thanh Vinh,Lyons, Demelza J.M.,Empel, Claire,Pace, Domenic P.,Dinh, An H.
, p. 12596 - 12606 (2020/11/18)
Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.
Superior activity and selectivity of multifunctional catalyst Pd-DTP@ZIF-8 in one pot synthesis of 3-phenyl propyl benzoate
Malkar, Radhika S.,Yadav, Ganapati D.
, p. 282 - 293 (2019/04/01)
The catalytic efficiency of zeolitic imidazolate framework (ZIF-8) has been explored by making it multifunctional. Dual active sites were incorporated such as acid (dodecatungstophosphoric acid, DTP) and metal (Pd°) to prepare 5% Pd-DTP@ZIF-8. DTP was encapsulated inside the cage of ZIF-8 by in-situ and bottle around the ship approach whereas Pd was loaded ex-situ by simple wet impregnation method. The catalytic efficiency was tested for one pot synthesis of 3-phenyl propyl benzoate (3-PPB), a perfumery compound, from cinnamyl alcohol and benzoic anhydride. Trans-esterification of cinnamyl alcohol with benzoic anhydride gives cinnamyl benzoate which on further hydrogenation gives 3-PPB. Three different supports were screened such as ZIF-8, K10 and MCF out of which ZIF-8 showed the maximum activity because of its high surface area and smaller pore diameter. Further Pd, Ni and Cu metals were studied for selective hydrogenation of C[dbnd]C bond among which 5% Pd-DTP@ZIF-8 gave almost 98% conversion of cinnamyl benzoate to 3-PPB with 93% selectivity. Fresh and spent catalysts were characterized by various techniques. 5% Pd-DTP@ZIF-8 showed anti-leaching property with great thermal stability. The turn over frequency and turn over number of the catalyst was observed to be 0.058 s?1 and 835, respectively. A kinetic model was developed with good fit using LHHW mechanism and the activation energy calculated as 17.45 kcal/mol for hydrogenation step. Thus, the reaction was found to be kinetically controlled. The entire process is green.
