19115-34-5Relevant articles and documents
Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates
Gava, Riccardo,Fuentes, M. Angeles,Besora, Maria,Belderrain, Tomas R.,Jacob, Kane,Maseras, Feliu,Etienne, Michel,Caballero, Ana,Perez, Pedro J.
, p. 2206 - 2210 (2014)
The reaction of esters with ethyl diazoacetate catalyzed by the complex [F27-Tp4Bo,3CF2CF3Ag(acetone)] generates α-(acyloxy)acetates in moderate to high yields. This is a novel transformation in the context of carbene-transfer reactions from diazo compounds that, according to experimental and theoretical data, is suggested to occur through zwitterionic intermediates.
Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids
Empel, Claire,Nguyen, Thanh Vinh,Koenigs, Rene M.
supporting information, p. 548 - 553 (2021/01/26)
Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).
In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters
Chen, Jijun,Shao, Ying,Ma, Liang,Ma, Meihua,Wan, Xiaobing
supporting information, p. 10723 - 10732 (2016/11/30)
A novel in situ generation of nitrilium from a nitrile ylide and the subsequent Mumm rearrangement of carboxylic acid, nitrile, and diazo compounds gave various unsymmetrical diacylglycine esters in moderate to high yields. This copper-catalyzed cascade reaction enables one-pot generation of two C-N bonds, one C=O bond, and one C-H bond, with nitrogen as the only byproduct. The reaction has a broad functional-group tolerance, is rapid, easily scales up to the 100 mmol scale, and is insensitive to air and moisture.
