Garnier Tony, Danel Mathieu, Magné Valentin, Pujol Anthony, Bénéteau Valérie, Pale Patrick, Chassaing Stefan
ITAV, Université de Toulouse, CNRS , Toulouse , France.
Laboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC) , Institut de Chimie, CNRS-UMR7177, Université de Strasbourg , 4 rue Blaise Pascal , 67070 Strasbourg , France.
J Org Chem. 2018 Jun 15;83(12):6408-6422. doi: 10.1021/acs.joc.8b00620. Epub 2018 May 29.
The copper(I)-doped zeolite Cu-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.
掺杂铜（I）的沸石Cu-USY被证明是一种适用于各种乌尔曼型偶联反应的多功能、高效且可回收的催化剂。这种催化材料易于制备且成本低廉，能够在无配体条件下实现多种O-、N-、S-和C-亲核试剂的芳基化和杂芳基化反应，同时展现出较大的官能团兼容性。通过全合成具有生物学相关性的天然二芳基醚3-甲基奥波伐醇，进一步证明了该催化剂促进C-O键形成的能力。从机理角度出发，根据亲核试剂的性质提出了两条相互竞争的途径，且与所得结果一致。
