14596-83-9Relevant articles and documents
PHOTOLYSES OF BIS(2-THIOPHENECARBONYL) AND BIS(3-THIOPHENECARBONYL) PEROXIDES IN BENZENE. PRODUCTION OF BIPHENYL FROM THE SOLVENT BENZENE CONTROLLED BY THE PHOTOLYSIS RATE
Urano, Toshiyuki,Kitamura, Akihide,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 867 - 870 (1983)
Direct and sensitized photolyses of bis(2-thiophenecarbonyl) (2-TPO) and bis(3-thiophenecarbonyl) peroxide (3-TPO) in benzene afforded biphenyl derived solely from the solvent among the products.The yield of biphenyl depended upon the rate with which the radical intermediates were generated from the peroxides in sufficiently high concentrations to dimerize.
Mechanistic Insight into Weak Base-Catalyzed Generation of Carbon Monoxide from Phenyl Formate and Its Application to Catalytic Carbonylation at Room Temperature without Use of External Carbon Monoxide Gas
Konishi, Hideyuki,Matsubara, Mika,Mori, Keisuke,Tokiwa, Takaki,Arulmozhiraja, Sundaram,Yamamoto, Yuta,Ishikawa, Yoshinobu,Hashimoto, Hiroshi,Shigeta, Yasuteru,Tokiwa, Hiroaki,Manabe, Kei
supporting information, p. 3592 - 3601 (2017/10/24)
The mechanisms of the weak base-catalyzed generation of carbon monoxide (CO) and phenol from phenyl formate were investigated by experimental and theoretical methods. Kinetic studies revealed a first-order reaction in both phenyl formate and the base. The reaction was found to proceed by an E2 α-elimination pathway, which involves the abstraction of the formyl proton of phenyl formate, simultaneously generating CO and phenoxide. The reaction rate was affected by the substituents on phenyl formate, the polarity of solvents, and the basicity of bases. The mechanistic insight obtained from these studies permitted the chemical control of the rate of CO generation, which was the key to the development of the external CO-free Pd-catalyzed phenoxycarbonylation of haloarenes at room temperature. Because of the mild reaction conditions and wide substrate scope, this phenoxycarbonylation constitutes a general, safe, and practical method to synthesize arenecarboxylic acid esters. (Figure presented.).
Palladium-catalyzed alkoxycarbonylation of aryl halides with phenols employing formic acid as the CO source
Qi, Xinxin,Li, Chong-Liang,Jiang, Li-Bing,Zhang, Wan-Quan,Wu, Xiao-Feng
, p. 3099 - 3107 (2016/05/24)
An efficient palladium-catalyzed alkoxycarbonylation of aryl halides with phenols has been developed. Various aryl benzoates have been isolated in good to excellent yields with formic acid as the CO source. The reaction proceeds smoothly under mild conditions and good functional group tolerance was observed.
