67962-25-8Relevant academic research and scientific papers
Direct reversible decarboxylation from stable organic acids in dimethylformamide solution
Kong, Duanyang,Moon, Patrick J.,Lui, Erica K.J.,Bsharat, Odey,Lundgren, Rylan J.
, p. 557 - 561 (2020/09/02)
Many classical and emerging methodologies in organic chemistry rely on carbon dioxide (CO2) extrusion to generate reactive intermediates for bond-forming events. Synthetic reactions that involve the microscopic reverse-the carboxylation of reactive intermediates-have conventionally been undertaken using very different conditions. We report that chemically stable C(sp3) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution. Decarboxylation-carboxylation occurs with substrates resistant to protodecarboxylation by Br?nsted acids under otherwise identical conditions. Isotopically labeled carboxylic acids can be prepared in high chemical and isotopic yield by simply supplying an atmosphere of 13CO2 to carboxylate salts in polar aprotic solvents. An understanding of carboxylate reactivity in solution enables conditions for the trapping of aldehydes, ketones, and a,b-unsaturated esters.
Heterogeneous visible-light-induced Meerwein hydration reaction of alkenes in water using mpg-C3N4 as a recyclable photocatalyst
Wang, Jingjing,Xue, Linshuang,Hong, Mei,Ni, Bangqing,Niu, Tengfei
supporting information, p. 411 - 416 (2020/02/13)
A green and efficient visible light induced Meerwein hydration reaction of alkenes in aqueous medium using mpg-C3N4 as a recyclabe photocatalyst has been disclosed. This protocol provides a direct approach for the preparation of racemic alcohols via a free radical mechanism. Water acted as both a solvent and a reagent without any additives or co-solvents. The metal-free heterogeneous semiconductor is found to be fully recyclable at least 5 times without any significant reduction in activity. The Meerwein hydration reaction has an excellent substrate scope and gave the desired products in moderate to high yields. Furthermore, this reaction could be carried out under solar light irradiation and is applicable for large-scale reactions with satisfactory results.
First TDAE Reactivity Using Benzonitrile Derivatives as Substrates and Its Application to the Synthesis of 3-Substituted Isochroman-1-ones
Khoumeri, Omar,Terme, Thierry,Vanelle, Patrice
, p. 2617 - 2623 (2018/05/03)
The first TDAE-initiated reaction between benzonitrile derivatives as substrates and substituted benzaldehydes to form substituted hydroxyethylbenzonitrile derivatives is reported. The 2-hydroxyethyl benzonitrile derivatives thus formed were good candidat
Regioselective ring-opening reaction of unsymmetrical 2,3-diaryl epoxides via catalytic hydrogenolysis with Pd(0)EnCatTM
Kimachi, Tetsutaro,Nagata, Hiroyo,Kobayashi, Yusuke,Takahashi, Kaori,Torii, Eri,Ju-Ichi, Motoharu
experimental part, p. 365 - 368 (2011/04/15)
A series of unsymmetrical 2,3-diaryl epoxides were hydrogenated under transfer-hydrogenation conditions using the polyurea-encapsulated palladium catalyst [Pd(0)EnCatTM]. The position of the cleaved C-O bond was determined by 1H NMR analysis of the ring-opened products derived from the epoxide, in which one of the two benzylic methyne protons is deuterated. The ratio of ring-opened products of the unsymmetrically substituted 2,3-diaryl epoxides was affected by the degree of the steric bulkiness on the aromatic ring. Georg Thieme Verlag Stuttgart New York.
