Synthesis of β,β-Disubstituted Indanones via the Pd-Catalyzed Tandem Conjugate Addition/Cyclization Reaction of Arylboronic Acids with α,β-Unsaturated Esters
Ang Gao, Xiu-Yan Liu, Hao Li, Chang-Hua Ding* and Xue-Long Hou*
*Shanghai Institute of Organic Chemistry, Chinese Academy of
Sciences, 345 Lingling Road, Shanghai 200032, China, Email: dingch
sioc.ac.cn,
xlhousioc.ac.cn
A. Gao, Y.-Y. Liu, H. Li, C.-H. Ding, X.-L. Hou, J. Org. Chem., 2017, 82, 9988-9994.
DOI: 10.1021/acs.joc.7b01364
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Abstract
The use of 2-(4,5-dihydroimidazol-2-yl)pyrimidine as ligand enables a Pd-catalyzed reaction of α,β-unsaturated esters with arylboronic acids to provide a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. The reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.
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proposed mechanism
Key Words
ID: J42-Y2017
