Wu Xian-Tao, Xiao En-Kai, Ma Feng, Yin Jin, Wang Jie, Chen Peng, Jiang Yi-Jun
School of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, People's Republic of China.
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Key Laboratory of Magnetic Resonance in Biological Systems, National Center for Magnetic Resonance in Wuhan, Innovation Academy for Precision Measurement Science and Technology, Chinese Academy of Sciences, Wuhan 430071, People's Republic of China.
J Org Chem. 2021 May 7;86(9):6734-6743. doi: 10.1021/acs.joc.1c00473. Epub 2021 Apr 14.
A general, efficient, and substrate-controlled regiodivergent trifluoroacetylation of carbazoles has been developed through Friedel-Crafts acylation. This strategy was applicable to a wide scope of readily available substituted carbazoles at air atmosphere without using a metal catalyst, affording the corresponding trifluoroacetylated carbazoles in up to 99% yield. The divergency of the products and the orientation rules have been illustrated based on different substituents on carbazole rings. This method could also be extended to the synthesis of chlorodifluoroacetylated and pentafluoropropionylated carbazoles, which have been achieved for the first time.
通过傅克酰基化反应，已开发出一种通用、高效且受底物控制的咔唑区域发散性三氟乙酰化反应。该策略适用于在空气氛围中无需使用金属催化剂的多种易于获得的取代咔唑，以高达99%的产率得到相应的三氟乙酰化咔唑。基于咔唑环上不同的取代基，已阐明了产物的发散性和取向规则。该方法还可扩展至氯二氟乙酰化和五氟丙酰化咔唑的合成，这是首次实现。
