Intramolecular metal-free oxidative aryl-aryl coupling: an unusual hypervalent-iodine-mediated rearrangement of 2-substituted N-phenylbenzamides.
Hypervalent-iodine-mediated oxidative coupling of the two aryl groups in either 2-acylamino-N-phenyl-benzamides or 2-hydroxy-N-phenylbenzamides, with concomitant insertion of the ortho-substituted N or O atom into the tether, has been described for the first time. This unusual metal-free rearrangement reaction involves an oxidative C(sp(2))-C(sp(2)) aryl-aryl bond formation, cleavage of a C(sp(2))-C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072 (China); Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072 (China).
Siyun
S
Shang
Daisy
D
Zhang-Negrerie
Yunfei
Y
Du
Kang
K
Zhao
D000147:Acids, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000147:Acids, Heterocyclic
cross-coupling; heterocycles; hypervalent iodine reagents; rearrangement