96829-91-3Relevant articles and documents
Synthesis of Acyl Fluorides via DAST-Mediated Fluorinative C-C Bond Cleavage of Activated Ketones
Kim, Danhee,Lim, Hee Nam
, p. 7465 - 7469 (2020/10/09)
A new protocol for preparation of acyl fluorides was developed by recognizing activated ketones as starting materials. The method provides a different scope compared with previously reported methods that employ carboxylic acids as substrates. A working hypothesis of pull-and-push-driven fluorinative C-C bond cleavage was successfully demonstrated by the simple addition of diethylaminosulfur trifluoride (DAST) derivatives to α-oximinoketones. The designed reaction system led to a highly efficient and chemoselective reaction. The wide availability of the ketones allowed for a range of synthetically useful aryloyl and aliphatic acyl fluorides including those containing chiral skeletons. The method is mild, fast, scalable, and potentially one-pot operative.
Catalytic C?H/C?F Coupling of Azoles and Acyl Fluorides
Ogiwara, Yohei,Iino, Yurika,Sakai, Norio
supporting information, p. 6513 - 6516 (2019/04/27)
A method for the palladium/copper-catalyzed direct acylation of azoles with acyl fluorides is described. This study reports the first examples of acyl fluorides being used as acylation reagents in transition-metal-catalyzed aromatic C?H bond functionalization reactions. Depending on the reaction temperature, decarbonylative coupling may also occur. Mechanistic studies suggest that the cleavage of the aromatic C?H bond, promoted by a copper-phosphine species, is not the rate-limiting step of this acylation.
Acylation of oxazoles by the copper-mediated reaction of oxazol-2-ylzinc chloride derivatives
Harn, Nancy K.,Gramer, Christine J.,Anderson, Benjamin A.
, p. 9453 - 9456 (2007/10/02)
C-2 acylation of oxazole derivatives is accomplished by reaction of oxazol-2-ylzinc chloride reagents with acid chlorides in the presence of cuprous iodide. O-acylated vinylisonitriles, which are the sole product from the corresponding reaction employing