34906-86-0Relevant articles and documents
One-pot route to new α,α-difluoroamides and α-ketoamides
Singh, Rajendra P.,Shreeve, Jean'ne M.
, p. 6063 - 6065 (2003)
New α,α-difluoroamides (4a-d, 6a-d) and α-ketoamides (5a-d, 7a-d) result from one-pot reactions of α-ketoacids, RCOCO2H (R = C6H5, CH3, CH3CH2, thienyl) (1a-d) with bis(2-methoxyethyl)aminosulfur trifluoride [(CH3-OCH2CH2)2NSF3] (2) (Deoxofluor) or diethylaminosulfur trifluoride [(CH3CH2)2NSF3)] (3) (DAST). Product yields depend on reaction times and the ratio of reagents used. Longer reaction times (～36 h) with a 1:2 ratio of α-ketoacids and 2 or 3 gave major yields of the α,α-difluoroamides, and shorter reaction times (～1 h) produced α,α-ketoamides as the major products. Reactants in a 1:1 ratio resulted in α-ketoamides only.
Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides
Yang, Shu-Qing,Yao, Yin-Qing,Chen, Xiao-Chao,Lu, Yong,Zhao, Xiao-Li,Liu, Ye
supporting information, p. 1032 - 1041 (2021/05/07)
The amino dicarbonylation of aryl halides affording α-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2(MeCN)2 and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and α-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2(MeCN)2-L4 catalytic system favors the amino dicarbonylation toward α-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.
Ligand-free Zn-catalyzed double carbonylation of aryl iodides with secondary amines: A simple and efficient approach to access α-ketoamides
Chidara, Sridhar,Mogili, Padma,Pitti, Vimala,Sarma Vangala, Markandeya
supporting information, (2021/12/22)
Herein, we report a Zinc catalyzed double carbonylation of aryl iodides with secondary amines under CO pressure for the synthesis of α-ketoamides in good to excellent yields. This methodology provides a simple and economic approach to derivatize useful α-
