Asymmetric Sonogashira C(sp3)–C(sp) bond coupling enabled by a copper(i) complex of a new guanidine-hybrid ligand?
Organic Chemistry Frontiers Pub Date: 2022-09-18 DOI: 10.1039/D2QO01283A
Abstract
A type of new chiral nitrogen-donor hybrid ligand bearing acyclic guanidine, amide, and pyridine subunits was rationalized for Cu(I)-catalyzed asymmetric Sonogashira C(sp3)–C(sp) cross-coupling. In connection with CuI, the reaction between diverse racemic secondary alkyl bromides and terminal alkynes proceeded smoothly to afford the coupling products in good outcomes (up to 96% yield and 95.5?:?4.5 er). The assembly of guanidine and pyridine with an amide linker is crucial for adjusting the redox ability of copper species, enabling efficient radical generation from alkyl bromides. The chiral ligands are easily accessible and readily modifiable using various amino acids and 2-picolylamine derivatives. This protocol provides new tools for copper salt-involved asymmetric radical transformations.
Recommended Literature
- [1] An analysis of the WTC fires using CIB correlations and simple modeling JGQuintiere 10.1177/0734904121989670
- [2] An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS? Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” KimLab Chip, 2006,6, 1213-1219 10.1039/B601954D
- [3] An investigation on the second-order nonlinear optical response of cationic bipyridine or phenanthroline iridium(iii) complexes bearing cyclometallated 2-phenylpyridines with a triphenylamine substituent? David B. Cordes,Alexandra M. Z. Slawin,Stefania Righetto,Denis Jacquemin,Eli Zysman-Colman,Véronique GuerchaisDalton Trans., 2018,47, 8292-8300 10.1039/C8DT00754C
- [4] An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis? Supaporn Sawadjoon,Joseph S. M. SamecOrg. Biomol. Chem., 2011,9, 2548-2554 10.1039/C0OB00383B
- [5] An Assessment of the Laminar Hypersonic Double-Cone Experiments in the LENS-XX Tunnel JaideepRay,PatrickBlonigan,EricT.Phipps,KathrynMaupin 10.2514/1.j062802
- [6] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [7] An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction? Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin JinJ. Mater. Chem. C, 2020,8, 192-200 10.1039/C9TC05297F
- [8] Aggregation dynamics, structure, and mechanical properties of bigels L. Di Michele,D. Fiocco,F. Varrato,E. Eiser,G. FoffiSoft Matter, 2014,10, 3633-3648 10.1039/C3SM52558A
- [9] An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. WoodEnergy Environ. Sci., 2018,11, 2784-2812 10.1039/C8EE01085D
- [10] An intramolecular tryptophan-condensation approach for peptide stapling? Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. JohannesOrg. Biomol. Chem., 2018,16, 389-392 10.1039/C7OB02667F
Journal Name：Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)