Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane

Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane

Let's avoid the risk! The title transformation has been developed for the synthesis of trifluoromethyl‐substituted cyclopropane derivatives (see scheme). It avoids the preparation of trifluoromethyl diazomethane and merges a number of areas: water as a reaction medium, iron catalysis, and acces...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) Vol. 49; no. 5; pp. 938 - 941
Main Authors: Morandi, Bill, Carreira, Erick M
Format: Journal Article
Language:English
Published: Weinheim Wiley-VCH Verlag 25-01-2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects:
alkenes
Alkenes - chemistry
Catalysis
cyclopropanation
Cyclopropanes - chemistry
Diazomethane - chemistry
Ethylamines - chemistry
homogeneous catalysis
iron
Iron - chemistry
Stereoisomerism
water
Water - chemistry
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Summary:Let's avoid the risk! The title transformation has been developed for the synthesis of trifluoromethyl‐substituted cyclopropane derivatives (see scheme). It avoids the preparation of trifluoromethyl diazomethane and merges a number of areas: water as a reaction medium, iron catalysis, and access to reactive intermediates under operationally safe conditions.
Bibliography:http://dx.doi.org/10.1002/anie.200905573
ArticleID:ANIE200905573
ark:/67375/WNG-WCFNZ5XW-C
We are grateful to the Swiss National Foundation and the Stipendienfonds der Schweizerischen Chemischen Industrie (SSCI) for a fellowship to B.M.
istex:6D0468B2572F30FC44B22CCFE6D55F126334E1E9
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200905573