Oxidative aromatic C-O bond formation: synthesis of 3-functionalized benzo[b]furans by FeCl3-mediated ring closure of alpha-aryl ketones.
A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl(3)-mediated intramolecular cyclization of electron-rich alpha-aryl ketones. The alkoxy substituent on the benzene ring in the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.
Liang
Zhidan
Z
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
Hou
Weizhe
W
Du
Yunfei
Y
Zhang
Yongliang
Y
Pan
Yan
Y
Mao
Deng
D
Zhao
Kang
K
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001572:Benzofurans; D002712:Chlorides; D005290:Ferric Compounds; D007659:Ketones; C024555:ferric chloride