Hydroxylation of organoborons via uranyl photocatalysis

作者：Jia, Yixin; Meng, Jiaolong; Hu, Deqing; Kang, Hao; Jiang, Xuefeng^*

来源：Organic Chemistry Frontiers, 2023, 10(11): 2688-2694.

DOI：10.1039/d3qo00468f

• OXIDATIVE HYDROXYLATION
• PHOTOREDOX CATALYSIS
• ARYLBORONIC ACIDS
• PHENOLS
• COMPLEX

Aerobic oxidation of organoboron, via uranyl photocatalysis using the principle of indirect single electron transfer (i-SET), was established under mild ambient conditions, and afforded multifarious phenols and alcohols, including nine natural products/pharmaceuticals. The i-SET process between the uranyl catalyst and triethylamine (Et3N), rather than through direct oxygen molecules (O-2), was determined through UV-visible absorption experiments, Stern-Volmer analysis, and density functional theory calculations. O-18 labeling experiments showed unambiguously that the oxygen was derived from O-2. The hundred-fold efficiency of a flow operation further demonstrated the potential for scaling up the application.

• 单位
  南开大学; 中国科学院