35665-26-0Relevant articles and documents
Dodecacarbonyltriruthenium catalyzed one-to-one addition of N-substituted formamides to olefins
Tsuji, Yasushi,Yoshii, Seiji,Ohsumi, Tatsuya,Kondo, Teruyuki,Watanabe, Yoshihisa
, p. 379 - 386 (1987)
Dodecacarbonyltriruthenium (Ru3(CO)12) showed high catalyitic activity for the first one-to-one addition of N-substituted formamides to both terminal and internal olefins at 180-200 deg C under a carbon monoxide pressure of 20 kg cm-2.The addit
Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides
Boyle, Mhairi,Livingstone, Keith,Henry, Martyn C.,Elwood, Jessica M. L.,Lopez-Fernandez, J. Daniel,Jamieson, Craig
supporting information, p. 334 - 338 (2022/01/20)
We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.
Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides
Matsumoto, Akira,Wang, Zhe,Maruoka, Keiji
, p. 5401 - 5411 (2021/04/12)
Herein, we describe a new approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically hindered amide bonds.
