Lin Zeng-Hui, Yao Yu-Fei, Zhang Cheng-Pan
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, China.
Org Lett. 2022 Nov 18;24(45):8417-8422. doi: 10.1021/acs.orglett.2c03541. Epub 2022 Nov 7.
Deuteration of arylthianthren-5-ium triflates with CDOD or CDOD/CDCOCD in the presence of CsCO by palladium catalysis or photoirradiation allowed the convenient synthesis of deuterated arenes in good yields. The Pd-catalyzed reaction generally gave better yields than the photoinduced deuteration, but exceptions also exist. They could complement each other in some cases. These reactions featured eco-friendly conditions, simplicity, inexpensive deuterium sources, good functional group tolerance, and a range of substrates. Since arylthianthren-5-ium salts could be readily synthesized from arenes and thianthrene 5-oxide, this protocol provided a formal aromatic C-H deuteration with high selectivity, enabling efficient deuterium labeling of multifunctionalized arenes and drug molecules.
在碳酸铯存在下，通过钯催化或光照射，用CDOD或CDOD/CDCOCD对芳基噻蒽-5-鎓三氟甲磺酸盐进行氘代反应，能够方便地以良好产率合成氘代芳烃。钯催化的反应通常比光诱导氘代反应产率更高，但也有例外情况。在某些情况下，它们可以相互补充。这些反应具有环境友好的条件、操作简单、氘源廉价、官能团耐受性好以及底物范围广等特点。由于芳基噻蒽-5-鎓盐可由芳烃和噻蒽5-氧化物轻松合成，该方法提供了具有高选择性的形式上的芳香族C-H氘代反应，能够对多官能化芳烃和药物分子进行高效的氘标记。
