Direct Dehydrogenative Access to Unsymmetrical Phenones

Abstract

The first non-directed dehydrogenative phenone coupling method of methylarenes with aromatic CÀ H bonds, displaying a large substrate scope, is herein reported. This reaction represents a far more direct atom-and step-efficient alternative to the classical Friedel-Crafts or Suzuki-Miyaura derived acylation reactions. The method can be carried out on a gram scale and was successfully applied to the synthesis of several Ketoprofen drug analogues.

Benzylic C-H Arylation with Dicyanoarenes via Convergent Paired-Electrolysis

“…16 Therefore, it appears that the present challenge would be to favour the coupling of the persistent aryl nitrile radical anion with the transient benzylic radical over the evolution of the latter into the corresponding benzylic alcohol that could lead to overoxidized products 5 or 6. 16,17 Results and discussion. To test, the feasibility of this approach, we selected ethyl biphenyl 1a and 1,4-dicyanobenzene 3a as substrates to generate 4a (Table 1).…”

Benzylic C–H arylation with dicyanoarenesviaconvergent paired electrolysis

“…Therefore, it appears that the present challenge would be to favour the coupling of the persistent aryl nitrile radical anion with the transient benzylic radical over the evolution of the latter into the corresponding benzylic alcohol that could lead to overoxidized products 5 or 6 . 16,17 Indeed, conducting the reaction in the absence of water or oxygen should prevent the evolution of A into a benzylic alcohol or ketone leading to 5 or 6 . However, the risk is that the highly reactive benzylic radical A and the corresponding carbocation resulting from further anodic oxidation would be involved in undesired reaction processes instead of reacting with the radical anion B .…”

Deselenylative Acylation and Nitration of Monoselenides

“…Given their importance in many fields, the development of methods for the construction of aroyl compounds has attracted a great deal of attention . However, the pursuit of environmentally benign and efficient synthetic approaches is still a challenge and has attracted continuous attention . Herein, we report the deselenylative acylation of monoselenides using acyl chloride/AgOTf as an efficient acylation reagent (Scheme e).…”