Phosphine-Catalyzed Difunctionalization of β-Fluoroalkyl α,β-Enones: A Direct Approach to β-Amino α-Diazo Carbonyl Compounds
Huamin Wang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorLi Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Search for more papers by this authorYoushao Tu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorRuiqi Xiang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yin-Long Guo
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
Search for more papers by this authorHuamin Wang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorLi Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Search for more papers by this authorYoushao Tu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorRuiqi Xiang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yin-Long Guo
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 P. R. China
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
Search for more papers by this authorDedicated to Professor Xiyan Lu on the occasion of his 90th birthday
Graphical Abstract
An efficient and practical phosphine-catalyzed vicinal difunctionalization of β-fluoroalkyl α,β-enones with TMSN3 has been developed. Meanwhile, the asymmetry variant induced by the nucleophilic bifunctional phosphine P4 led to various chiral fluoroalkylated β-amino α-diazocarbonyl compounds in high yields and enantioselectivity.
Abstract
An efficient and practical phosphine-catalyzed vicinal difunctionalization of β-fluoroalkyl α,β-enones with TMSN3 has been developed. Using dppb as the catalyst, the reaction worked efficiently to yield various β-amino α-diazocarbonyl compounds in high yields (up to 94 %). This work marks the first efficient construction of α-diazocarbonyl compounds by phosphine catalysis. Meanwhile, the asymmetric variant induced by the nucleophilic bifunctional phosphine P4 led to various chiral fluoroalkylated β-amino α-diazocarbonyl compounds in high yields and enantioselectivity. NMR and ESI-MS studies support the existence of the key reaction intermediates. In contrast, β-azide carbonyl compounds would be furnished in good yields from β-fluoroalkylated β,β-disubstituted enones.
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