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Letter

Samarium Triflate-Catalyzed Halogen-Promoted Friedel−Crafts Alkylation with Alkenes

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Saumen Hajra,* Biswajit Maji, and Sukanta Bar

Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India

Org. Lett., 2007, 9 (15), pp 2783–2786

DOI: 10.1021/ol070813t

Publication Date (Web): June 22, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A versatile and efficient halogen-promoted highly regio- and stereoselective Friedel−Crafts (F-C) alkylation with alkenes has been developed with use of easily available and inexpensive NBS or I₂ as the efficient halogen sources. Lewis acids, in particular metal triflates, are found to be effective catalysts for this halogen-promoted F-C alkylation. Among these, Sm(OTf)₃ was the best catalyst. Electron-rich arenes smoothly underwent F-C alkylation with a variety of alkenes including α,β-unsaturated carbonyl compounds.

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Published In Issue July 19, 2007
Received April 5, 2007

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Letter

Samarium Triflate-Catalyzed Halogen-Promoted Friedel−Crafts Alkylation with Alkenes

Abstract

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Recommend & Share

Related Content

Intramolecular Nitrile Oxide−Alkene Cycloaddition of Sugar Derivatives with Unmasked Hydroxyl Group(s)

Catalytic Thia-Sommelet−Hauser Rearrangement: Application to the Synthesis of Oxindoles

Nickel-Catalyzed C–H/C–O Coupling of Azoles with Phenol Derivatives

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