AI Article Synopsis
Article Abstract
A direct metal-free amination of arylalkynes has been developed, which proceeds by reaction of the terminal alkyne with the hypervalent iodine reagent PhI(OAc)NTs(2) within a single-step operation. This unprecedented intermolecular C-H to C-N bond conversion provides rapid access to the important class of ynamides. In addition to the title reaction, the related transformation between alkylated alkynes and the iodine(III) reagent is also discussed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ja306211q | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Crystal structure of bis-{5-(4-chloro-phen-yl)-3-[6-(1-pyrazol-1-yl)pyridin-2-yl]-1-1,2,4-triazol-1-ido}nickel(II) methanol disolvate.
Acta Crystallogr E Crystallogr Commun
October 2024
Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv, 01601, Ukraine.
The unit cell of the title compound, [Ni(CHClN)]·2CHOH, consists of a neutral complex and two methanol mol-ecules. In the complex, the two tridentate 2-(3-(4-chloro-phen-yl)-1-1,2,4-triazol-5-yl)-6-(1-pyrazol-1-yl)pyridine ligands coordinate to the central Ni ion through the N atoms of the pyrazole, pyridine and triazole groups, forming a pseudo-octa-hedral coordination sphere. Neighbouring tapered mol-ecules are linked through weak C-H(pz)⋯π(ph) inter-actions into monoperiodic chains, which are further linked through weak C-H⋯N/C inter-actions into diperiodic layers.
View Article and Find Full Text PDFProgrammable Synthesis of Cationic Azaperylenes via Rh(III)-Catalyzed Multiple C-H/N-H Bonds Activation and Annulation.
Org Lett
December 2024
Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China.
Rh(III)-catalyzed dual N-H and triple C-H activation/(4 + 2) annulation of 2-aryl-2,3-dihydro-1-perimidines and alkynes has been disclosed to construct 4,5,14,15-tetrasubstituted cationic azaperylenes with high yields (up to 95%) and broad scope. Tandem (4 + 2) annulation of 1-perimidines with vinylene carbonate and alkynes affords 4,5-disubstituted azaperylene salts, and -alkynyl 1-perimidines undergo an intra- and intermolecular annulation cascade to give 4,5,14-trisubstituted targets. Most of the intermediates were detected by ESI-MS, indicating a convincible mechanism including three possible paths.
View Article and Find Full Text PDFFerrocenyl amines as directing groups for C-H activation have limitations as they are prone to undergo oxidation, allylic deamination, and β-hydride elimination. The fundamental challenge observed here is the competition between the desired C-H activation the vulnerable β-C-H bond activation of amines and fine-tuning of a suitable oxidant which avoids the oxidation of the β-C-H bond and ferrocene. Herein, the potential of an axially chiral NOBINAc ligand is revealed to implement the enantioselective Pd-catalyzed C-H activation process of ferrocenyl amines.
View Article and Find Full Text PDFControllable Synthesis of Benzo[]furo[2,3-]azepines or Furo[3,2-]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C-H Amination Reactions.
J Org Chem
December 2024
School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People's Republic of China.
Two novel Pd-catalyzed protocols for the controllable synthesis of benzo[]furo[2,3-]azepines and furo[3,2-]indoles have been developed by intermolecular oxidative annulation of 2-(furan-2-yl)anilines and propargyl carbonates versus intramolecular C-H amination reactions. These two protocols feature great scalability, functional group tolerance, and relatively mild reaction conditions. Notably, the robust methodologies could also provide valuable opportunities for assembling azepine-fused benzothiophene, indole-fused benzothiophene, and indole-fused benzimidazole, which may have potential applications in the synthesis of related pharmaceuticals or polymeric materials.
View Article and Find Full Text PDFPalladium-Catalyzed Dual C-H Arylation/Cyclization Reaction of Iodoferrocenes with -Bromobenzamides for the Construction of Arylated Isoquinolone-Fused Ferrocenes.
J Org Chem
December 2024
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
We reported a palladium/norbornene-catalyzed dual intermolecular C-H arylation/intramolecular cyclization reaction of iodoferrocenes with -bromobenzamides, enabling the formation of arylated isoquinolone-fused ferrocenes in a straightforward and effective manner. This method has a broad substrate scope and good functional group compatibility, while the gram-scale reaction demonstrates the practicality of this method.
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!