Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. I.

DOI: 10.1016/S0040-4020(98)00930-2

Source and publish data:

Tetrahedron p. 14869 - 14884 (1998)

Update date:2022-08-02

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Authors:

Cerezo, Silvia

Cortes, Jordi

Moreno-Manas, Marcial

Pleixats, Roser

Roglans, Anna

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Article abstract of DOI:10.1016/S0040-4020(98)00930-2

Arenesulfonamides, sulfamide, and cyanamide are efficiently allylated using allylic carbonates under Pd(0)-catalysis. N-Arenesulfonyl-2,5- dihydropyrroles are obtained by ruthenium-mediated ring closing metathesis of the corresponding N-diallylated compounds. A stereochemical study of the reactions of ethyl cis-(5-methyl-2-cyclohexenyl) carbonate with 2,4,6- triisopropylphenylsulfonamide was performed, clean overall retention of configuration being found with bidentate phosphines.

Full text of DOI:10.1016/S0040-4020(98)00930-2

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