Copper-Catalyzed Coupling of Acyl Chlorides with gem-Difluorinated Organozinc Reagents via Acyl Dithiocarbamates

A cross-coupling of acyl chlorides with gem-difluorinated organozinc reagents affording difluorinated ketones is described. In the reaction, acyl chlorides are first treated with potassium dithiocarbamate to generate S-acyl dithiocarbamates, which couple with organozincs in the presence of a copper­...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 1; pp. 478 - 483
Main Authors Ashirbaev, Salavat S, Levin, Vitalij V, Struchkova, Marina I, Dilman, Alexander D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.01.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
DIFLUOROMETHYLATION
PRACTICAL SYNTHESIS
ACID
DIFLUOROCARBENE
ARYL HALIDES
FLUORINE
METAL CATALYSIS
ORGANOMETALLICS
ELECTROPHILES
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Summary:A cross-coupling of acyl chlorides with gem-difluorinated organozinc reagents affording difluorinated ketones is described. In the reaction, acyl chlorides are first treated with potassium dithiocarbamate to generate S-acyl dithiocarbamates, which couple with organozincs in the presence of a copper­(I) catalyst.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02598