使用水合氯醛和（杂）芳基硼酸酯通过钯催化合成1-（杂）芳基-2,2,2-三氯乙醇
Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines.
作者信息
Shimizu Minori, Okuda Yuta, Toyoda Koki, Akiyama Ryo, Shinozaki Hiraku, Yamamoto Tetsuya
机构信息
Department of Materials and Life Sciences, Tokyo Denki University 5 Senju-Asahicho Adachi Tokyo 120-8551 Japan
Department of Materials Science and Engineering, Tokyo Denki University 5 Senju-Asahicho, Adachi-ku Tokyo 120-8551 Japan.
出版信息
RSC Adv. 2021 May 18;11(29):17734-17739. doi: 10.1039/d1ra02403e. eCollection 2021 May 13.
1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols. Notably, PhS-IPent-CYP which coordinated the bulky yet flexible 2,6-di(pentan-3-yl)aniline (IPent)-based NHC showed good catalytic activities and promoted the transformation in 24-97% yields.
1-（杂）芳基-2,2,2-三氯乙醇是合成各种生物活性化合物的重要关键中间体。在此，我们描述了N-杂环卡宾（NHC）配位的环金属化钯配合物（CYP）催化水合氯醛与（杂）芳基硼酸酯的（杂）芳基加成反应，为1-（杂）芳基-2,2,2-三氯乙醇提供了一种新的合成方法。值得注意的是，与庞大而灵活的基于2,6-二（戊-3-基）苯胺（IPent）的NHC配位的PhS-IPent-CYP表现出良好的催化活性，并以24-97%的产率促进了该转化反应。
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