A convenient copper-catalyzed intra-/intermolecular diamination of β,γ-unsaturated hydrazones has been developed with simple amines as external amine sources. The protocol enables efficient access to various nitrogen-containing pyrazolines under mild reaction conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b03401 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper-Catalyzed Hydrogen Production through the Dehydrogenative Coupling of Methanol and Diamine.
Precis Chem
April 2024
Beijing National Laboratory for Molecular Sciences, New Cornerstone Science Laboratory, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
A hydrogen storage system was developed via heterogeneous catalysis, employing the dehydrogenative coupling of methanol and ,'-dimethylethylenediamine to efficiently produce high-purity H. In this process, the Cu/ZnO/AlO catalyst displayed superior activity in hydrogen production, with Cu identified as the major active site through comprehensive characterization.
View Article and Find Full Text PDFCopper-Catalyzed Enantioselective Hydrophosphorylation of Unactivated Alkynes.
Angew Chem Int Ed Engl
January 2025
State Key Laboratory of Medical Chemical Biology, College of Pharmacy, Nankai University, 38 Tongyan Road, Jinnan District, 300350, Tianjin, P. R. China.
P-stereogenic phosphorus compounds are essential across various fields, yet their synthesis via enantioselective P-C bond formation remains both challenging and underdeveloped. We report the first copper-catalyzed enantioselective hydrophosphorylation of alkynes, facilitated by a newly designed chiral 1,2-diamine ligand. Unlike previous methods that rely on kinetic resolution with less than 50 % conversion, our approach employs a distinct dynamic kinetic asymmetric transformation mechanism, achieving complete conversion of racemic starting materials.
View Article and Find Full Text PDFCopper-Catalyzed Diamination of Alkenes using -Benzoylhydroxylamines to Access the Four Azaindoline Families.
Org Lett
October 2024
Department of New Drug Discovery and Development, Chungnam National University, Daejeon 34134, Korea.
A mild and efficient method for the copper-catalyzed diamination of alkenes is described. In this reaction, -benzoylhydroxylamine serves as an electrophilic nitrogen source for the regioselective formation of C-N bonds. This transformation provides a novel strategy for synthesizing all four isomeric 2,3-disubstituted azaindoline families and offers a wide substrate scope.
View Article and Find Full Text PDFCopper-Catalyzed α-Alkylation of Aryl Acetonitriles with Benzyl Alcohols.
J Org Chem
October 2024
Laboratory of Organic Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece.
A highly efficient, formed CuCl/TMEDA catalytic system (TMEDA = ,,','-tetramethylethylene-diamine) for the cross-coupling reaction of aryl acetonitriles with benzyl alcohols is reported. This user-friendly protocol, employing a low catalyst loading and a catalytic amount of base, leads to the synthesis of α-alkylated nitriles in up to 99% yield. Experimental mechanistic investigations reveal that the key step of this transformation is the C(sp)-H functionalization of the alcohol, taking place a hydrogen atom abstraction, with the simultaneous formation of copper-hydride species.
View Article and Find Full Text PDFCopper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions.
J Am Chem Soc
September 2024
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, Massachusetts 02139, United States.
We report a mild method for the copper-catalyzed amination of aryl chlorides. Key to the success of the method was the use of highly sterically encumbered ,-diaryl diamine ligands which resist catalyst deactivation, allowing reactions to proceed at significantly lower temperatures and with a broader scope than current protocols. A sequence of highly chemoselective C-N and C-O cross-coupling reactions were demonstrated, and mechanistic studies indicate that oxidative addition of the Cu catalyst to the aryl chlorides is rate-limiting.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!