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Addition of Amines to Nitriles Catalyzed by Ytterbium Amides: An Efficient One-Step Synthesis of Monosubstituted N-Arylamidines
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Abstract

A one-step synthesis of monosubstituted N-arylamidinates via addition of amines to nitriles catalyzed by ytterbium amides is reported. The reactions with various substrates give the products in good to excellent yields with 5 mol % ytterbium at 100 °C under solvent-free conditions.
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

N-Allyl-N-sulfonyl Ynamides as Synthetic Precursors to Amidines and Vinylogous Amidines. An Unexpected N-to-C 1,3-Sulfonyl Shift in Nitrile Synthesis
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Kyle A. DeKorver, Whitney L. Johnson, Yu Zhang, Richard P. Hsung, Huifang Dai, Jun Deng, Andrew G. Lohse, and Yan-Shi ZhangThe Journal of Organic Chemistry2011 Article ASAPA detailed study of amidine synthesis from N-allyl-N-sulfonyl ynamides is described here. Mechanistically, this is a fascinating reaction consisting of diverging pathways that could lead to deallylation or allyl transfer depending upon the oxidation state ...

Influence of Schiff Base and Lanthanide Metals on the Synthesis, Stability, and Reactivity of Monoamido Lanthanide Complexes Bearing Two Schiff Bases
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Fubin Han, Qiaoqiao Teng, Yong Zhang, Yaorong Wang, and Qi ShenInorganic Chemistry2011 50 (6), 2634-2643The monoamido lanthanide complexes stabilized by Schiff base ligand L2LnN(TMS)2 (L = 3,5-But2-2-(O)-C6H2CH═N-8-C9H6N, Ln = Yb (1), Y (2), Eu (3), Nd (4), and La (5)) were synthesized in good yields by the reactions of Ln[N(TMS)2]3 with 1.8 equiv of HL in ...

Ligand-Free Copper-Catalyzed Arylation of Amidines
Michelle Cortes-Salva, Corey Garvin, and Jon C. AntillaThe Journal of Organic Chemistry2011 76 (5), 1456-1459Ligand-Free Copper-Catalyzed Arylation of Amidines
Michelle Cortes-Salva, Corey Garvin, and Jon C. AntillaThe Journal of Organic Chemistry2011 76 (5), 1456-1459Copper-catalyzed cross-coupling reactions of amidine salts were utilized to synthesize monoarylated amidines in moderate to high yields with ligand-free conditions. DMF was the superior solvent for the N-arylation of benzamidines, while MeCN was used in ...

Catalytic Acylation of Amines with Aldehydes or Aldoximes
C. Liana Allen, Simge Davulcu, and Jonathan M. J. WilliamsOrganic Letters2010 12 (22), 5096-5099Catalytic Acylation of Amines with Aldehydes or Aldoximes
C. Liana Allen, Simge Davulcu, and Jonathan M. J. WilliamsOrganic Letters2010 12 (22), 5096-5099The simple nickel salt NiCl2·6H2O catalyzes the coupling of aldoximes with amines to give secondary or tertiary amide products. The aldoxime can be prepared in situ from the corresponding aldehyde. The use of 18O-labeled oximes has allowed insight into ...

Reactions of an Aluminum Amide with Aromatic Nitriles: Formation of Al−N−C Frameworks
K. Maheswari, N. M. Rajendran, Jens Meyer and N. Dastagiri ReddyOrganometallics2010 29 (17), 3799-3807Reactions of an Aluminum Amide with Aromatic Nitriles: Formation of Al−N−C Frameworks
K. Maheswari, N. M. Rajendran, Jens Meyer and N. Dastagiri ReddyOrganometallics2010 29 (17), 3799-3807Reactions of a four-membered Al−N ring, [(Dipp)HNAlMe2]2 (2; Dipp =2,6-diisopropylphenyl), with the aromatic nitriles PhCN, TbpCN (Tbp =4-tert-butylphenyl), DmpCN (Dmp = 2,6-dimethylphenyl), DepCN (DepCN = 2,6-diethylphenyl), and DippCN are reported. 2 ...
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History
- Published In Issue February 07, 2008
- Received November 14, 2007
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