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Highly Atom Efficient Guanylation of both Aromatic and Secondary Amines Catalyzed by Simple Lanthanide Amides
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Section:Abstract
It is demonstrated that the cyclopentadienyl-free simple lanthanide amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 (Ln = La, Sm, Eu, Y, Yb) and Ln[N(SiMe3)2]3 (Ln = Y, Yb) are highly efficient catalysts for the guanylation of both aromatic and secondary amines with a high activity under mild conditions. It is found that these catalysts are compatible with a wide range of solvents and substrates.
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This article has been cited by 23 ACS Journal articles (5 most recent appear below).
One-Pot Synthesis and Unpredicted Hydrogen Bonds of the Guanidinium Triflates from Readily Available Amines, Carbodiimides, and Zn(OTf)2
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Dongzhen Li, Yang Wang, Wen-Xiong Zhang, Shaoguang Zhang, Jie Guang, and Zhenfeng XiOrganometallics2011 30 (19), 5278-5283The first synthesis of trisubstituted guanidinium triflates has been achieved by a simple one-step procedure from readily available amines, carbodiimides, and Zn(OTf)2. X-ray analysis revealed they adopt 1-D chain-like or novel 3-D hydrogen-bonded ...
Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)3(THF)2 (Ln: Lanthanide and Yttrium) and Ln(OAr)3(THF)2 as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group
Yang Cao, Zhu Du, Wenbo Li, Junmei Li, Yong Zhang, Fan Xu, and Qi ShenInorganic Chemistry2011 50 (8), 3729-3737Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)3(THF)2 (Ln: Lanthanide and Yttrium) and Ln(OAr)3(THF)2 as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group
Yang Cao, Zhu Du, Wenbo Li, Junmei Li, Yong Zhang, Fan Xu, and Qi ShenInorganic Chemistry2011 50 (8), 3729-3737Reaction of Ln(OAr1)3(THF)2 (Ar1= [2,6-(tBu)2-4-MeC6H2] with carbodiimides (RNCNR) in toluene afforded the RNCNR coordinated complexes (Ar1O)3Ln(NCNR) (R = iPr (isopropyl), Ln = Y (1) and Yb (2); R = Cy (cyclohexyl), Ln = Y (3)) in high yields. Treatment ...
Fast Synthesis of Hydrazine and Azo Derivatives by Oxidation of Rare-Earth-Metal−Nitrogen Bonds
Lijun Zhang, Jing Xia, Qinghai Li, Xihong Li, and Shaowu WangOrganometallics2011 30 (3), 375-378Fast Synthesis of Hydrazine and Azo Derivatives by Oxidation of Rare-Earth-Metal−Nitrogen Bonds
Lijun Zhang, Jing Xia, Qinghai Li, Xihong Li, and Shaowu WangOrganometallics2011 30 (3), 375-378A novel N−N coupling reaction was developed through the oxidation of rare-earth-metal−nitrogen bonds produced by treatment of the easily available rare-earth-metal amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with aromatic primary or secondary amines. The reaction ...
Highly Efficient Aluminum-Catalyzed Hydro-amination/-hydrazination of Carbodiimides
Jürgen Koller and Robert G. BergmanOrganometallics2010 29 (22), 5946-5952Highly Efficient Aluminum-Catalyzed Hydro-amination/-hydrazination of Carbodiimides
Jürgen Koller and Robert G. BergmanOrganometallics2010 29 (22), 5946-5952The catalytic activity of commercially available [Al(NMe2)3]2 (1) and a dimethyl aluminum guanidinate complex toward the hydro-amination/-hydrazination of carbodiimides was studied. The guanidinate-supported complex 2 was prepared via salt metathesis ...
Lanthanide Amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 Catalyzed Hydrophosphonylation of Aryl Aldehydes
Qingmao Wu, Jun Zhou, Zhigang Yao, Fan Xu, and Qi ShenThe Journal of Organic Chemistry2010 75 (21), 7498-7501Lanthanide Amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 Catalyzed Hydrophosphonylation of Aryl Aldehydes
Qingmao Wu, Jun Zhou, Zhigang Yao, Fan Xu, and Qi ShenThe Journal of Organic Chemistry2010 75 (21), 7498-7501A highly efficient method for the synthesis of α-hydroxy phosphonates via lanthanide amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 catalyzed hydrophosphonylation of aromatic aldehydes was developed. The reactions produced the products in excellent yields in the ...
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History
- Published In Issue August 31, 2007
- Received May 1, 2007
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