alpha-Halo carbonyls enable meta selective primary, secondary and tertiary C-H alkylations by ruthenium catalysis

A catalytic meta selective C-H alkylation of arenes is described using a wide range of alpha-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substi...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 28; pp. 5993 - 6000
Main Authors Paterson, Andrew J., Heron, Callum J., McMullin, Claire L., Mahon, Mary F., Press, Neil J., Frost, Christopher G.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 19.07.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECTING GROUP
FUNCTIONALIZATION
OLEFINATION
BROMINATION
ARYLATION
ARENES
SULFONATION
BOND ACTIVATION
LIGAND
CARBOXYLIC-ACIDS
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Summary:A catalytic meta selective C-H alkylation of arenes is described using a wide range of alpha-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(II) complex activates the substrate molecule and is responsible for the meta selectivity observed. A distinct second activation of the coupling partner allows site selective reaction between both components.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01192j