Attachment of carbonyl functionalities onto olefins via copper-promoted radical reaction of dichloromethylcyanides

Chemo- and regioselective protocols for attachment of various carbonyl functionalities onto unactivated olefins have been developed. Atom transfer radical reactions of Cl3CCN, Cl2C(R)CN, and Cl2C(CN)2 were all promoted efficiently by a catalytic amount of CuCl and 1,1′-bis(diphenylphosphino)ferrocen...

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Bibliographic Details
Published inTetrahedron Vol. 68; no. 26; pp. 5290 - 5296
Main Authors Kamijo, Shin, Yokosaka, Shinya, Inoue, Masayuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.07.2012
Elsevier
Subjects
Attachment
Carbonyl functionality
Carbonyls
Chemistry
Chemistry, Organic
Chlorides
Conversion
Copper catalysis
Esters
Ketones
Olefin
Olefins
Physical Sciences
Radical reaction
Radicals
Science & Technology
Carbonyl functionality
Olefin
Radical reaction
Copper catalysis
ORGANIC-SYNTHESIS
CROSS-METATHESIS
CATALYZED ADDITION
REAGENTS
EFFICIENT PROCEDURE
MALONONITRILE
CHLORIDES
DERIVATIVES
CYCLIZATION
EQUIVALENT
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Summary:Chemo- and regioselective protocols for attachment of various carbonyl functionalities onto unactivated olefins have been developed. Atom transfer radical reactions of Cl3CCN, Cl2C(R)CN, and Cl2C(CN)2 were all promoted efficiently by a catalytic amount of CuCl and 1,1′-bis(diphenylphosphino)ferrocene to introduce chloromethylcyanide and chloride units to the C–C double bonds. Conversion of the chloromethylcyanide to the carbonyl functionalities (e.g., aldehydes, ketones and esters), and subsequent double bond reconstruction through elimination of HCl resulted in selective formation of the carbonyl-conjugated E-olefins. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.01.089