Synthesis of Substituted Benzenes via Bi(OTf)₃-Mediated Intramolecular Carbonyl Allylation of α-Prenyl or α-Geranyl β-Arylketosulfones

Meng-Yang Chang*, Yu-Chieh Cheng and Yi-Ju Lu

*Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Email: mychangkmu.edu.tw

M.-Y. Chang, Y.-C. Cheng, Y.-J. Lu, Org. Lett., 2015, 17, 3142-3145.

DOI: 10.1021/acs.orglett.5b01461

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Abstract

Intramolecular carbonyl allylation of α-prenyl β-arylketosulfones in the presence of molecular sieves affords substituted benzenes in good yields via Bi(OTf)₃-mediated annulation followed by a sequential desulfonative aromatization. The use of α-geranyl β-arylketosulfones enables the synthesis of tetrahydronaphthalenes.

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Key Words

cyclizations

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ID: J54-Y2015