Department of Chemistry, Centre of Advanced Study, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
J Org Chem. 2021 Dec 17;86(24):17884-17895. doi: 10.1021/acs.joc.1c02194. Epub 2021 Dec 8.
Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect the coupling, and no need of complete exclusion of oxygen was experienced in the presence of glycohybrid triazole ligand High product yields were obtained at 130 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted aromatic halides including 9-bromo noscapine. In contrast, at room temperature, a very low loading of the Cu catalytic system could produce excellent yields in Glaser coupling including homocoupling and heterocoupling of a variety of aliphatic and aromatic alkynes.
糖基三唑已被引入作为 Cu 催化的 Sonogashira 反应的有效配体，以克服 Cu 催化中侧向同偶联反应的挑战。在密封管中，大气中的氧气不会影响偶联，并且在糖基杂化三唑配体的存在下，不需要完全排除氧气[1]。在 130°C 下，各种底物包括脂肪族和芳香族末端炔烃以及不同取代的芳基卤化物包括 9-溴那可丁都获得了高产率。相比之下，在室温下，Cu 催化体系的非常低的负载量可以在包括各种脂肪族和芳香族炔烃的 Glaser 偶联中产生优异的产率，包括同偶联和异偶联。
[1] Glycosyl Triazoles as Ligands in Copper-Catalyzed Cross-Coupling Reactions. Org. Lett. 2011, 13, 2060-2063.
