Preparation of Allyl Sulfoxides by Palladium-Catalyzed Allylic Alkylation of Sulfenate Anions

Palladium-catalyzed allylic alkylation of sulfenate anions, generated from β-sulfinylesters by retro-Michael reaction, can take place under biphasic conditions. This new reaction provides a simple, mild, and efficient route to allyl sulfoxides in good yields.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 71; no. 19; pp. 7449 - 7454
Main Authors Maitro, Guillaume, Prestat, Guillaume, Madec, David, Poli, Giovanni
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.09.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
OXIDATION
THIOLS
ENANTIOENRICHED SULFOXIDES
PHASE-TRANSFER CATALYSIS
STEREOSELECTIVE-SYNTHESIS
INDUCTION
PARA-TOLYL SULFONES
SALTS
1-ALKYNYL SULFOXIDES
SULFINYLZINCATION
Michael addition
Anions
Catalytic reaction
Transition element complexes
Sulfenate
Sulfoxide
Palladium complex
Platinoid Complexes
Chemical synthesis
Alkylation
Allylic compound
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Summary:Palladium-catalyzed allylic alkylation of sulfenate anions, generated from β-sulfinylesters by retro-Michael reaction, can take place under biphasic conditions. This new reaction provides a simple, mild, and efficient route to allyl sulfoxides in good yields.
Bibliography:ark:/67375/TPS-2QD18S1P-4
istex:EF499912E8F39D47BEE7632ED5D705F336687C59
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061359u