Kamitani Miharu, Nakayasu Bunta, Fujimoto Hayato, Yasui Kosuke, Kodama Takuya, Tobisu Mamoru
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives, Osaka University, Suita, Osaka 565-0871, Japan.
Science. 2023 Feb 3;379(6631):484-488. doi: 10.1126/science.ade5110. Epub 2023 Feb 2.
Single-carbon atom transfer reactions are lacking in organic synthesis, partly because of the absence of atomic carbon sources under standard solution-phase conditions. We report here that N-heterocyclic carbenes can serve as atomic carbon donors through the loss of a 1,2-diimine moiety. This strategy is applicable to single-carbon atom transfer to α,β-unsaturated amides, which can be converted into homologated γ-lactams through the formation of four single bonds to one carbon center in one operation.
单碳原子转移反应在有机合成中较为缺乏，部分原因是在标准溶液相条件下缺乏原子碳源。我们在此报告，氮杂环卡宾可通过失去一个1,2 - 二亚胺部分作为原子碳供体。该策略适用于将单碳原子转移至α,β - 不饱和酰胺，通过一步形成与一个碳中心的四个单键，α,β - 不饱和酰胺可转化为同系化的γ - 内酰胺。
