Less Is More: N(BOH)2 Configuration Exhibits Higher Reactivity than the B3NO2 Heterocycle in Catalytic Dehydrative Amide Formation
Less Is More: N(BOH)2 Configuration Exhibits Higher Reactivity than the B3NO2 Heterocycle in Catalytic Dehydrative Amide Formation
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DOI：
10.1021/acs.orglett.2c04382
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发表时间：
2023-01-20
期刊：
影响因子：
5.2
通讯作者：
Kumagai, Naoya
中科院分区：
文献类型：
--
作者：
Opie, Christopher R.;Noda, Hidetoshi;Kumagai, Naoya
二硼子结构已成为羧酸和胺催化脱水酰胺化的有前景的支架。这封信描述了第一个可分离的 N(BOH)2 化合物作为酰胺化催化剂的设计、合成和评估。新型催化剂在周转频率方面优于之前报道的 B3NO2 杂环催化剂，尽管前者在接触胺时会逐渐分解。这项工作为设计更好的直接酰胺化催化剂开辟了一条途径。
Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.