Baeyer-Villiger Oxidation 拜耳-维利格氧化
Baeyer-Villiger氧化是羰基附近碳-碳键的氧化断裂,羰基将酮转化为酯,将环酮转化为内酯。Baeyer-Villiger可以用过酸(如MCBPA)或过氧化氢和路易斯酸进行。
反应的区域特异性取决于羰基上取代基的相对迁移能力。能够稳定正电荷的取代基更容易迁移,因此优先顺序为:叔。烷基>环己基>秒。烷基>苯基>普里姆。烷基>CH3。在某些情况下,立体电子或环应变因素也影响区域化学结果。
Baeyer-Villiger氧化机理
相关反应
Related Reactions
Dakin Reaction
Recent Literature
Baeyer-Villiger Oxidation of Ketones to Esters with Sodium Percarbonate/Trifluoroacetic Acid
G. A. Olah, Q. Wang, N. J. Trivedi, G. K. S. Prakash, Synthesis, 1991, 739-740.
Selenoxides as Catalysts for Epoxidation and Baeyer-Villiger Oxidation with Hydrogen Peroxide
M. A. Goodman, M. R. Detty, Synlett, 2006, 1100-1104.
Hypervalent λ3-Bromane Strategy for Baeyer-Villiger Oxidation: Selective Transformation of Primary Aliphatic and Aromatic Aldehydes to Formates, Which is Missing in the Classical Baeyer-Villiger Oxidation
Y. Yoshida, K. Murakami, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc., 2010, 132, 9236-9239.
General Metal-Free Baeyer-Villiger-Type Synthesis of Vinyl Acetates
B. Poladura, A. Martínez-Castañeda, H. Rodríguez-Solla, R. Llavona, C. Concellón, V. del Amo, Org. Lett., 2013, 15, 2810-2813.
Enantioselective Baeyer-Villiger Oxidation: Desymmetrization of Meso Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones
L. Zhou, X. H. Liu, J. Ji, Y. H. Zhang, X. L. Hu, L. L. Lin, X. M. Feng, J. Am. Chem. Soc., 2012, 134, 17023-17026.
Asymmetric Baeyer-Villiger Reaction with Hydrogen Peroxide Catalyzed by a Novel Planar-Chiral Bisflavin
S. Murahashi, S. Ono, Y. Imada, Angew. Chem. Int. Ed., 2002, 41, 2366-2368.
Conversion of Cyclic Acetals to Hydroxy Esters by MCPBA Oxidation
J. Y. Kim, H. Rhee, M. Kim, J. Korean Chem. Soc., 2002, 46, 479-483.