5338-49-8Relevant articles and documents
Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis
Chen, Yilin,Du, Jianbo,Zuo, Zhiwei
supporting information, p. 266 - 279 (2020/01/08)
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Heterogeneous CeO2 catalyst for the one-pot synthesis of organic carbamates from amines, CO2 and alcohols
Honda, Masayoshi,Sonehara, Satoru,Yasuda, Hiroshi,Nakagawa, Yoshinao,Tomishige, Keiichi
scheme or table, p. 3406 - 3413 (2012/01/15)
Heterogeneous CeO2 catalyst can catalyze the one-pot synthesis of methyl benzylcarbamate from benzylamine, CO2 and methanol. The yield of methyl benzylcarbamate reached 92% at >99% benzylamine conversion and 92% benzylamine-based selectivity even in the absence of the dehydrating agents. The catalyst is reusable after the calcination at 873 K for 3 h. Various carbamates can be synthesized with good yield and high selectivity by the reaction of amines + CO2 + alcohols over CeO2. The main formation route of methyl benzylcarbamate is suggested to be the reaction of dimethyl carbonate or the precursor of dimethyl carbonate formation with benzylamine.
Pd-catalyzed N-arylation of secondary acyclic amides: Catalyst development, scope, and computational study
Hicks, Jacqueline D.,Hyde, Alan M.,Cuezva, Alberto Martinez,Buchwald, Stephen L.
supporting information; experimental part, p. 16720 - 16734 (2010/04/04)
We report the efficient N-arylation of acyclic secondary amides and related nucleophiles with aryl nonaflates, triflates, and chlorides. This method allows for easy variation of the aromatic component in tertiary aryl amides. A new biaryl phosphine with P-bound 3,5-(bis)trifluoromethylphenyl groups was found to be uniquely effective for this amidation. The critical aspects of the ligand were explored through synthetic, mechanistic, and computational studies. Systematic variation of the ligand revealed the importance of (1) a methoxy group on the aromatic carbon of the "top ring" ortho to the phosphorus and (2) two highly electron-withdrawing P-bound 3,5-(bis)trifluoromethylphenyl groups. Computational studies suggest the electron-deficient nature of the ligand is important in facilitating amide binding to the LPd(II)(Ph)(X) intermediate.