Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp³ C–H bonds with molecular oxygen

Abstract

A ligand-free iron-catalyzed method for the oxygenation of benzylic sp3 C–H bonds by molecular oxygen (1 atm) using a thiyl radical as a cocatalyst has been developed.

An efficient and practical aerobic oxidation of benzylic methylenes by recyclable N-hydroxyimide

“…These results offer a new option for synthesizing (di)benzo(hetero)cyclic ketones. Also, different from most reported iron-catalyzed ligand-free liquid aerobic oxidations, 9,15 chain-alkyl benzene are oxidized with high yields (more than 80%) in this system (2i–2j). Remarkably, EB derivatives with mild and strong electron-withdrawing group (EWG) can transformed to ketones with excellent yields in comparatively mild conditions (2k–2o), which distinguish this methodology from most reported NHIs-catalyzed benzylic aerobic oxidations.…”

Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

“…Using the same procedure, we have synthesized two other ibuprofen hybrids already described in the literature in order to evaluate and compare their potential biological properties with the newly obtained ibuprofen hybrid 8. We obtained the 1-(3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-isobutylphenyl)propan-1-one 9 [16], and 2-(4-isobutylphenyl)-1-(piperidin-1yl)propan-1-one 10 [17,18] (Figure 4).…”

Selective Degradation of Styrene‐Related Plastics Catalyzed by Iron under Visible Light**

“…Earth-abundant metals were found to transform alkanes to alcohols and ketones under oxygen atmosphere. [24][25][26][27][28][29][30][31][32][33] In addition, CÀ C bond scission of alcohols and ketones through alkoxyl radical intermediates applying inexpensive catalysts were reported recently. [34][35][36][37][38][39][40][41][42][43] Despite limitations, these results illustrate the possibility of developing an economic system for oxidative CÀ C bond cleavage in an environmentally friendly way (Figure 1b).…”