Keck Science Department, Scripps, Claremont McKenna and Pitzer Colleges, Claremont, California 91711, United States.
University of Michigan, Ann Arbor, Michigan 48109, United States.
J Org Chem. 2020 Oct 16;85(20):13256-13263. doi: 10.1021/acs.joc.0c01552. Epub 2020 Oct 5.
A silver-catalyzed protocol was found to afford the -formylation of amines in moderate-to-good yields. Ethylene glycol-derived, oligomeric ethers were found to function as the formylating agent, with 1,4-dioxane affording the best results. This reaction does not require the use of stoichiometric activating reagents, and avoids the use of explosive reagents or toxic gases, such as CO, as the C1 synthon. Mechanistic studies indicate a single-electron transfer-based pathway. This work highlights the ability of silver to participate in unexpected reaction pathways.
一种银催化的方法被发现可以中等至良好的产率实现胺的甲酰化。乙二醇衍生的齐聚醚被发现是有效的甲酰化试剂，其中 1,4-二氧六环的效果最好。该反应不需要使用化学计量的活化试剂，并且避免了使用 CO 等爆炸试剂或有毒气体作为 C1 合成子。机理研究表明该反应遵循单电子转移途径。这项工作突出了银参与意料之外的反应途径的能力。
