Metal- and Chemical-Oxidant-Free CH/CH Cross-Coupling of Aromatic Compounds: The Use of Radical-Cation Pools

Pool and couple: A method for oxidative CH/CH cross‐coupling has been developed using “radical‐cation pools”. Aromatic compounds react with aryl radical cations, which are generated and accumulated by low‐temperature electrolysis (see scheme). This method avoids both the nonselective oxidation of...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 29; pp. 7259 - 7262
Main Authors Morofuji, Tatsuya, Shimizu, Akihiro, Yoshida, Jun-ichi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.07.2012
WILEY‐VCH Verlag
Wiley
Subjects
Aromatic compounds
Cations
Chemistry
Chemistry, Multidisciplinary
CC coupling
CH activation
electrochemistry
Electrolysis
Joining
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Pools
radical ions
Radicals
Science & Technology
ELECTROLYSIS
CARBON
electrochemistry
radical ions
oxidation
BOND FORMATION
C?H activation
C?C coupling
NON-NUCLEOPHILIC MEDIA
SIMPLE ARENES
FUNCTIONALIZATION
CATALYZED ORTHO-ARYLATION
NAPHTHALENE
GENERATION
DERIVATIVES
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Summary:Pool and couple: A method for oxidative CH/CH cross‐coupling has been developed using “radical‐cation pools”. Aromatic compounds react with aryl radical cations, which are generated and accumulated by low‐temperature electrolysis (see scheme). This method avoids both the nonselective oxidation of substrates and oxidation of products and effects the CH/CH cross‐coupling of aromatic compounds without metal complexes and chemical oxidants.
Bibliography:Ministry of Education, Culture, Sports, Science & Technology (Japan)
FUNDP
istex:73DE50D183112BD367059F1EF29AD60CBB90ECBF
ArticleID:ANIE201202788
ark:/67375/WNG-P5LNHNN6-4
We thank the Ministry of Education, Culture, Sports, Science & Technology (Japan) for a Grant-in-Aid for Scientific Research on Innovative Areas, Organic Synthesis Based on Reaction Integration Development of New Methods and Creation of New Substances (2105). We also thank Prof. Benoît Champagne in Facultés Universitaires Notre-Dame de la Paix (FUNDP), Belgium for the use of computers and the program for the theoretical calculations.
We thank the Ministry of Education, Culture, Sports, Science & Technology (Japan) for a Grant‐in‐Aid for Scientific Research on Innovative Areas, Organic Synthesis Based on Reaction Integration Development of New Methods and Creation of New Substances (2105). We also thank Prof. Benoît Champagne in Facultés Universitaires Notre‐Dame de la Paix (FUNDP), Belgium for the use of computers and the program for the theoretical calculations.
KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201202788