Trifluoromethyl- and Fluoroalkylselenolations of Alkynyl Copper(I) Compounds.

Chemistry

Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, 43 Bd du 11 Novembre 1918, 69622, Villeurbanne, France.

Published: July 2017

The successful perfluoroalkylselenolation of alkynyl copper(I) compounds is described herein. The reaction occurs under oxidant free conditions at room temperature. This convenient one-pot procedure is based on the in situ generation of trifluoromethylselenyl chlorides. The developed system shows high functional group tolerance and also promotes the employment of fluoroalkyl derivatives.

Download full-text PDF

Source
http://dx.doi.org/10.1002/chem.201702028DOI Listing

Publication Analysis

Top Keywords

alkynyl copperi
8
copperi compounds
8
trifluoromethyl- fluoroalkylselenolations
4
fluoroalkylselenolations alkynyl
4
compounds successful
4
successful perfluoroalkylselenolation
4
perfluoroalkylselenolation alkynyl
4
compounds described
4
described reaction
4
reaction occurs
4

Similar Publications

Planar chirality found tremendous use in many fields, such as chemistry, optics, and materials science. In particular, planar chiral [2.2]paracyclophanes (PCPs) are a type of structurally interesting and practically useful chiral compounds bearing unique electronic and photophysical properties and thus have been widely used in π-stacking polymers, organic luminescent materials, and as a valuable toolbox for developing chiral ligands or organocatalysts.

View Article and Find Full Text PDF

The pursuit of precision in the engineering of metal nanoparticle assemblies has long fascinated scientists, but achieving atomic-level accuracy continues to pose a significant challenge. This research sheds light on the hierarchical assembly processes of two high-nuclearity Cu(I) nanoclusters (NCs). By employing a multiligand cooperative stabilization strategy, we have isolated a series of thiacalix[4]arene (TC4A)/alkynyl coprotected Cu(I) NCs (, where = , , , ).

View Article and Find Full Text PDF

Structural diversity of copper(I) alkynyl cluster-based coordination polymers utilizing bifunctional pyridine carboxylic acid ligands.

Nanoscale

October 2024

State Key Laboratory of Materials Processing and Die & Mould Technology, School of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan 430074, China.

The utilization of bifunctional ligands, specifically pyridine carboxylic acids, endowed with dual coordination sites, has been instrumental in the assembly of polymer materials. The ambidentate characteristics of these ligands play a crucial role in shaping the structure and framework of cluster-based polymers. In this study, we have synthesized a diverse array of multidimensional copper(I) alkynyl cluster-based polymers (CACPs) by employing four distinct pyridine carboxylic acids - namely, isonicotinic acid (INA), 6-isoquinolinecarboxylic acid (IQL), 4-pyridin-4-yl-benzoic acid (4-PyBA), and 3-pyridin-4-yl-benzoic acid (3-PyBA) - as linking ligands.

View Article and Find Full Text PDF

In this study, the reaction between 2-(3,5-dimethylpyrazolylmethyl)-5-(dimethylaminomethyl)pyrrole and thiophenol under heating conditions afforded the new ligand 2-(3,5-dimethylpyrazolylmethyl)-5-(phenylthiomethyl)pyrrole 2. The reaction of 2 with -chloroperbenzoic acid provided sulfoxide 3 and sulfone 4 group-containing ligands. The reaction of 2 with copper(I) halides provided the binuclear complexes [Cu(μ-X){μ-CHN-2-(CHMepz)-5-(CHSPh)-κ-S,N}] (X = Cl, Br and I, 5-7) in high yields.

View Article and Find Full Text PDF

Synthesis of Indole-Fused Pyrazino[1,2-a]quinazolinones by Copper(I)-Catalyzed Selective Hydroamination-Cyclization of Alkynyl-tethered Quinazolinones.

Chemistry

September 2024

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, 541004, Guilin, China.

We described a copper(I)-catalyzed atom economic and selective hydroamination-cyclization of alkynyl-tethered quinazolinones to prepare a variety of indole-fused pyrazino[1,2-a]quinazolinones in good to excellent yields ranging from 39 %-99 % under mild reaction conditions. Control experiments revealed that coordination-directed method of quinazolinone moiety with copper(I) was important for the selective hydroamination-cyclization of alkynes at the N1-atom instead of N3-atom of quinazolinone. The reaction could be easily performed at gram scales and some prepared indole-fused pyrazino[1,2-a]quinazolinones with donating groups on the indole moiety showed a distinct fluorescence emission wavelength with blue shift under the acid conditions.

View Article and Find Full Text PDF

Want 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!