3132-15-8Relevant academic research and scientific papers
Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights
Li, Li,Song, Feifei,Zhong, Xiumei,Wu, Yun-Dong,Zhang, Xinhao,Chen, Jiean,Huang, Yong
supporting information, p. 126 - 132 (2019/11/28)
Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).
Water-Soluble Acylating Agents: Preparation of 2-Acylthio-1-alkylpyridinium Salts and Acylation of Phenols, Acids, and/or Amines with These Salts in an Aqueous Phase
Sakakibara, Tohru,Watabe, Yukie,Yamada, Masahide,Sudoh, Rokuro
, p. 247 - 254 (2007/10/02)
Reaction of phenols, amines, and acids with 2-benzoylthio-1-methylpyridinium chloride prepared in situ from benzoyl chloride and 1-methyl-2(1H)-pyridinethione, afforded the corresponding benzoyl derivatives in good yields.In the reaction of p-nitrophenol, even catalytic amount of 1-methyl-2(1H)-pyridinethione proved to be effective.Similar reactions of p-nitrophenol with isobutyryl chloride and acetyl chloride in the presence of 1-methyl-2(1H)-pyridinethione afforded p-nitrophenyl isobutyrate and p-nitrophenyl acetate in 63 and 44percent yields, respectively. 2-Benzoylthio-, 2-acetylthio-, and 2-isobutyrylthio-1-ethylpyridinium tetrafluorobora tes were prepared by treatment of the corresponding 2-acylthiopyridines with triethyloxonium tetrafluoroborate.These pyridinium salts also acted as acylating agents in an aqueous phase. some competitive reactions of 2-aminoethanol and phenols with 2-benzoylthio-1-methylpyridinium chloride were also investigated.
