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

Sílvia Cerezo; Jordi Cortés; Marcial Moreno-Mañas; Roser Pleixats; Anna Roglans

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

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

Sílvia Cerezo, Jordi Cortés, Marcial Moreno-Mañas, Roser Pleixats, Anna Roglans

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

53 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	14869-14884
Journal	Tetrahedron
Volume	54
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(98)00930-2
Publication status	Published - 3 Dec 1998

Keywords

Allylation
Catalysis
Palladium
Stereochemistry

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

abstract = "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.",

keywords = "Allylation, Catalysis, Palladium, Stereochemistry",

author = "S{\'i}lvia Cerezo and Jordi Cort{\'e}s and Marcial Moreno-Ma{\~n}as and Roser Pleixats and Anna Roglans",

year = "1998",

month = dec,

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doi = "10.1016/S0040-4020(98)00930-2",

language = "English",

volume = "54",

pages = "14869--14884",

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TY - JOUR

T1 - Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. I.

AU - Cerezo, Sílvia

AU - Cortés, Jordi

AU - Moreno-Mañas, Marcial

AU - Pleixats, Roser

AU - Roglans, Anna

PY - 1998/12/3

Y1 - 1998/12/3

N2 - 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.

AB - 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.

KW - Allylation

KW - Catalysis

KW - Palladium

KW - Stereochemistry

U2 - 10.1016/S0040-4020(98)00930-2

DO - 10.1016/S0040-4020(98)00930-2

M3 - Article

VL - 54

SP - 14869

EP - 14884

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 49

ER -