An Bohang, Cui Hao, Zheng Chao, Chen Ji-Lin, Lan Feng, You Shu-Li, Zhang Xiao
Fujian Key Laboratory of Polymer Materials, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University Fuzhou 350007 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences Shanghai 200032 China
Chem Sci. 2024 Feb 6;15(11):4114-4120. doi: 10.1039/d4sc00120f. eCollection 2024 Mar 13.
C-H functionalization and dearomatization constitute fundamental transformations of aromatic compounds, which find wide applications in various research areas. However, achieving both transformations from the same substrates with a single catalyst by operating a distinct mechanism remains challenging. Here, we report a photocatalytic strategy to modulate the reaction pathways that can be directed toward either C-H functionalization or dearomatization under redox-neutral or net-reductive conditions, respectively. Two sets of indoles and indolines bearing tertiary alcohols are divergently furnished with good yields and high selectivity. The key to success is the introduction of isoazatruxene ITN-2 as a novel photocatalyst (PC), which outperforms the commonly used PCs. The ready synthesis and high modulability of isoazatruxene type PCs indicate their great application potential.
碳-氢官能团化和去芳构化是芳香族化合物的基本转化反应，在各个研究领域都有广泛应用。然而，通过独特的反应机制，使用单一催化剂从相同底物实现这两种转化仍然具有挑战性。在此，我们报道了一种光催化策略，可分别在氧化还原中性或净还原条件下调节反应途径，使其分别导向碳-氢官能团化或去芳构化。两组带有叔醇的吲哚和二氢吲哚以良好的产率和高选择性被分别合成出来。成功的关键在于引入异氮杂金刚烷ITN-2作为新型光催化剂（PC），它优于常用的光催化剂。异氮杂金刚烷型光催化剂易于合成且具有高度可调节性，这表明它们具有巨大的应用潜力。
