Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.
College of Chemistry and Environment Engineering, Baise University, Baise 533000, China.
Org Lett. 2022 Aug 5;24(30):5608-5613. doi: 10.1021/acs.orglett.2c02328. Epub 2022 Jul 26.
A palladium-catalyzed deuterated formylation of aryl sulfonium salts is prepared conveniently from readily available arenes, which enables the expedient synthesis of a series of structurally diverse C-1 deuterated aldehydes with 96%-99% deuterium incorporation. The easy to handle and cost-effective DCOONa provides a deuterium source, which can be introduced onto the formyl units with excellent selectivity under the palladium-catalytic redox neutral conditions. This catalytic route can accomplish the direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C (sp)-H thianthrenation. Moreover, on the basis of this practical approach, several deuterated drugs and analogues could be prepared with excellent levels of deuterium incorporation.
钯催化的芳基锍盐氘代甲酰化反应方便地从易得的芳基化合物制备，使一系列结构多样的 C-1 氘代醛的简便合成成为可能，氘的掺入率达到 96%-99%。易于处理和具有成本效益的 DCOONa 提供了氘源，在钯催化的氧化还原中性条件下，它可以极好的选择性地引入到甲酰基单元中。该催化途径可以在 C(sp)-H 噻蒽化辅助下，直接对生物活性分子和天然产物衍生物进行后期 C-H 官能化。此外，在此实用方法的基础上，可通过该方法制备几种具有优异氘掺入水平的氘代药物和类似物。
