57673-91-3Relevant academic research and scientific papers
Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, p. 5342 - 5347 (2021/06/30)
A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.
Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)?H Compounds
Tan, Chen,Liu, Xinyuan,Jia, Huanxin,Zhao, Xiaowen,Chen, Jian,Wang, Zhiyong,Tan, Jiajing
supporting information, p. 881 - 887 (2020/01/02)
Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)?H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)?H compounds.
Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton-Todd Reaction under Base-Free Conditions
Kaboudin, Babak,Donyavi, Atousa,Kazemi, Foad
, p. 170 - 174 (2017/09/28)
A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton-Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.
Cross-hetero-dehydrogenative coupling reaction of phosphites: A catalytic metal-free phosphorylation of amines and alcohols
Dhineshkumar, Jayaraman,Prabhu, Kandikere Ramaiah
supporting information, p. 6062 - 6065 (2014/01/06)
Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as a catalyst and H2O2 as the sole oxidant under mild reaction conditions. This method provides an easy route for synthesizing a variety of phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates which are of biological importance.
An activated phosphate for an efficient amide and peptide coupling reagent
Yasuhara, Tomohisa,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 2901 - 2902 (2007/10/03)
An activated phosphate for an efficient amide and peptide coupling reagent was discussed. Activation of diethyl phosphates was realized by attaching trifluoromethanesulfonanilide as an efficient leaving group and the phosphate proved to be a promising amide and peptide coupling reagent. Results showed that reactions of a primary amine with α-branched carboxylic acids and benzoic acid gave within 1 h the amides in quite high yield.
Two-carbon homologation of Grignard reagents to primary amines
Osowska-Pacewicka, Krystyna,Zwierzak, Andrzej
, p. 333 - 335 (2007/10/03)
A novel, convenient synthesis of N-(diethoxyphosphoryl)aziridine is described. Application of this compound as a synthetic equivalent of an a2 type synthon for aminoethylation of Grignard reagents is demonstrated.
Novel organophosphorus reagents for the synthesis of amines
Zwierzak, Andrzej,Osowska-Pacewicka, Krystyna
, p. 569 - 572 (2007/10/03)
New organophosphorus equivalents of a2 type N-protected amine synthons are presented.
PO-Activated Olefination and Conversion of Aldehydes and Ketones to Higher Amines; II. Synthesis of Arylethylamines
Heymes, A.,Chekroun, I.
, p. 245 - 249 (2007/10/02)
The transformation of arylcarboxaldehydes and/or - ketones 2 by three different routes into arylethylamines 3 and/or 4 is reported.According to the first route, the intermediate iminophosphonates 9 react through a classical PO-activated olefination.The second and the third involve the rearrangement of the iminophosphonates 9 into the vinylphosphoramidates 12.
