Rhodium-catalyzed direct oxidative carbonylation of aromatic C-H bond with CO and alcohols.
A general protocol for the rhodium-catalyzed oxidative carbonylation of arenes to form esters has been developed. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic arenes, and the reaction shows wide functional group tolerance and excellent regioselectivities. Up to 96% yield of ortho-substituted aryl or heteroaryl carboxylic esters were obtained with this methodology. The possible mechanism for the rhodium-catalyzed oxidative carbonylation reaction was proposed in this article. Studies show that Oxone play an important role in the transformation.
Guan
Zheng-Hui
ZH
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Ren
Zhi-Hui
ZH
Spinella
Stephen M
SM
Yu
Shichao
S
Liang
Yong-Min
YM
Zhang
Xumu
X
D000438:Alcohols / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry; D013464:Sulfuric Acids / Q000737:chemistry
D000438:Alcohols; D001555:Benzene Derivatives; D001565:Benzoates; D004952:Esters; D013464:Sulfuric Acids; D002248:Carbon Monoxide; D012238:Rhodium; C048813:potassium peroxymonosulfuric acid