288093-73-2Relevant academic research and scientific papers
Direct Amidation of Esters by Ball Milling**
Barreteau, Fabien,Battilocchio, Claudio,Browne, Duncan L.,Godineau, Edouard,Leitch, Jamie A.,Nicholson, William I.,Payne, Riley,Priestley, Ian
supporting information, p. 21868 - 21874 (2021/09/02)
The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.
Nickel-Catalyzed Amide Bond Formation from Methyl Esters
Ben Halima, Taoufik,Masson-Makdissi, Jeanne,Newman, Stephen G.
supporting information, p. 12925 - 12929 (2018/09/14)
Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.
Systematic study on the catalytic synthesis of unsaturated 2-ketocarboxamides: Palladium-catalyzed double carbonylation of 1-iodocyclohexene
Carrilho, Rui M.B.,Pereira, Mariette M.,Takács, Attila,Kollár, László
experimental part, p. 204 - 207 (2012/01/05)
1-Iodocyclohexene, a benchmark substrate, has been double carbonylated in the presence of palladium-phosphite precatalysts. Triarylphosphites with OR substituents, able to act both as P-monodentate and hemilabile P,O-heterobidentate ligands were used in t
Tandem alkylation-cyclization process via an O,C-dianion
Banaag, April R.,Berger, Gideon O.,Dhoro, Francis,Delos Santos, Derrick B.,Dixon, Darryl D.,Mitchell, James P.,Tokeshi, Bradley K.,Tius, Marcus A.
, p. 3419 - 3428 (2007/10/03)
A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the γ carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6.
