Synthesis of β,β-Disubstituted Indanones via the Pd-Catalyzed Tandem Conjugate Addition/Cyclization Reaction of Arylboronic Acids with α,β-Unsaturated Esters

Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)­pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mecha...

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Published inJournal of organic chemistry Vol. 82; no. 19; pp. 9988 - 9994
Main Authors Gao, Ang, Liu, Xiu-Yan, Li, Hao, Ding, Chang-Hua, Hou, Xue-Long
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.10.2017
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Summary:Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)­pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01364