Catalytic O-H bond insertion reactions using surface modified sewage sludge as a catalyst

作者：Zhang, Zhipeng; Yu, Yang; Huang, Fei^*; Yi, Xiangyan; Xu, Yao; He, Yide; Baell, Jonathan B.; Huang, He^*

来源：Green Chemistry, 2020, 22(5): 1594-1604.

DOI：10.1039/c9gc03428e

• WET AIR OXIDATION
• ARYL-ALPHA-DIAZOACETATES
• FENTON-LIKE DEGRADATION
• SI-H
• CARBENE INSERTION
• NATURAL-PRODUCTS
• DIAZO-COMPOUNDS
• N-H
• HYDROGEN-ATOM
• M-CRESOL

Developing a greener, sustainable catalyst is a very important but challenging task in organic synthesis. Herein, for the first time, we choose more economical and greener surface modified sewage sludge-derived carbonaceous materials (SW) treated by perchloric acid as a new catalyst for carbene insertion of alpha-aryl alpha-diazoacetates into O-H bonds of phenols with good yields and high functional group tolerance. Significantly, we explored the scope of natural phenols with compelling biological activity, and successfully afforded the O-H insertion and meta C-H functionalization products. Their structures have been confirmed by single-crystal X-ray crystallography. Furthermore, the bioactivities (anti-tumor and anti-inflammatory) of the majority of O-H insertion products are better than those of the natural phenols themselves. The IC50 values indicated that the remarkable compounds 7a (IC50 = 16.80 mu M) and 7c (IC50 = 16.48 mu M) had better inhibition for tumor cell A-549 than positive control DDP (IC50 = 20.62 mu M). It should be noted that these transformations may provide a new strategy to derive natural products and discover new drugs.

• 单位
  1; 苏州大学