Mild ArI-Catalyzed C(sp2)H or C(sp3)H Functionalization/CO Formation: An Intriguing Catalyst-Controlled Selectivity Switch

A tandem C(sp2)H and C(sp3)H functionalization/CO bond formation catalyzed by iodine(III) reagents generated in situ has been developed. The method shows wide scope under mild conditions and exhibits an unprecedented selectivity profile that can be switched depending on the catalyst employed. Who...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 53; no. 41; pp. 11084 - 11087
Main Authors Wang, Xueqiang, Gallardo-Donaire, Joan, Martin, Ruben
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 06.10.2014
WILEY‐VCH Verlag
Wiley
Subjects
Bonding
Catalysts
Chemistry
Chemistry, Multidisciplinary
Control equipment
CH functionalization
domino reactions
Formations
homogeneous catalysis
Iodine
metal-free reactions
Physical Sciences
Science & Technology
Selectivity
site selectivity
Switches
Transformations
OXIDATION
REAGENTS
C-O
metal-free reactions
BOND FORMATION
C-H functionalization
M-CHLOROPERBENZOIC ACID
homogeneous catalysis
ACETOXYLATION
LACTONES
domino reactions
CHEMISTRY
LACTONIZATION
site selectivity
CARBOXYLIC-ACIDS
CH functionalization
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Summary:A tandem C(sp2)H and C(sp3)H functionalization/CO bond formation catalyzed by iodine(III) reagents generated in situ has been developed. The method shows wide scope under mild conditions and exhibits an unprecedented selectivity profile that can be switched depending on the catalyst employed. Who controls the switch? I! A tandem C(sp2)H or C(sp3)H functionalization/CO bond‐forming reaction catalyzed by IIII reagents generated in situ has been developed. The transformation shows broad scope under mild conditions and exhibits an unprecedented selectivity profile that can be switched depending on the nature of the iodine catalyst employed (see scheme; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol).
Bibliography:ArticleID:ANIE201407011
MINECO - No. CTQ2012-34054
European Research Council - No. ERC-277883
ark:/67375/WNG-1V6LFWM6-T
istex:5647B08757C1C91A5983D79B7A677792E9372FD1
We thank the ICIQ Foundation, the European Research Council (ERC-277883), and MINECO (CTQ2012-34054) for support. Johnson Matthey, Umicore, and Nippon Chemical Industrial are acknowledged for a gift of metal and ligand sources. J.G.-D. thanks MICINN for a FPI fellowship. Dr. A. Correa, A. Shafir, and Prof. K. Muñiz are gratefully acknowledged for insightful discussions.
ICIQ Foundation
We thank the ICIQ Foundation, the European Research Council (ERC‐277883), and MINECO (CTQ2012‐34054) for support. Johnson Matthey, Umicore, and Nippon Chemical Industrial are acknowledged for a gift of metal and ligand sources. J.G.‐D. thanks MICINN for a FPI fellowship. Dr. A. Correa, A. Shafir, and Prof. K. Muñiz are gratefully acknowledged for insightful discussions.
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201407011