College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, China.
Org Lett. 2023 May 5;25(17):2970-2974. doi: 10.1021/acs.orglett.3c00735. Epub 2023 Apr 23.
Condition-dependent transformations between hydroximic acids and thioacetic acid were achieved. Using NHHCO in the ethanol solvent, efficient N-O bond cleavage of hydroxamic acids occurred to afford primary amides with high functional group compatibility. The reaction was switched to -acylation when NEt and HO were used as the base and solvent, respectively. These facile transformations could be scaled up to the gram level smoothly. Preliminary mechanistic studies suggested that the N-O bond cleavage involves a cascade process of acylation/reduction.
实现了羟肟酸和硫代乙酸之间的条件依赖性转化。在乙醇溶剂中使用 NHHCO，羟肟酸的高效 N-O 键断裂发生，得到具有高官能团相容性的伯酰胺。当使用 NEt 和 HO 分别作为碱和溶剂时，反应转变为 -酰化。这些简便的转化可以顺利地放大到克级规模。初步的机理研究表明，N-O 键断裂涉及酰化/还原的级联过程。
