School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
Org Lett. 2023 Jun 16;25(23):4298-4302. doi: 10.1021/acs.orglett.3c01336. Epub 2023 Jun 7.
The synthesis of functionalized carbazoles as privileged nitrogen heterocycles has emerged as a central topic in drug discovery and material science. We herein disclose the rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones and 2-methylidene cyclic carbonate as an allylating surrogate, resulting in the formation of C2-formylated carbazoles via tandem C-H allylation, [3 + 2] cycloaddition, aromatization, and benzylic oxidation. The synthetic utility of this protocol is highlighted by a variety of post-transformations of C2-formylated carbazoles.
作为药物发现和材料科学的核心主题，功能化咔唑的合成已经出现。我们在此公开了铑(III)催化的吲哚基亚硝酮与 2-亚甲基环碳酸酯之间的交叉偶联反应，作为烯丙基取代基，通过串联 C-H 烯丙基化、[3 + 2]环加成、芳构化和苄基氧化，形成 C2-甲酰化咔唑。该协议的合成实用性通过 C2-甲酰化咔唑的各种后转化得到了强调。
