Para-Selective, Iridium-Catalyzed C–H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions

Para C–H borylations (CHB) of tetraalkylammonium sulfates and sulfamates have been achieved using bipyridine-ligated Ir boryl catalysts. Selectivities can be modulated by both the length of the alkyl groups in the tetraalkylammonium cations and the substituents on the bipyridine ligands. Ion pairing...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-10, Vol.141 (39), p.15483-15487
Main Authors: Montero Bastidas, Jose R, Oleskey, Thomas J, Miller, Susanne L, Smith, Milton R, Maleczka, Robert E
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Benzyl Alcohol - chemistry
Catalysis
Iridium - chemistry
Models, Molecular
Molecular Structure
Phenols - chemistry
Static Electricity
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Summary:Para C–H borylations (CHB) of tetraalkylammonium sulfates and sulfamates have been achieved using bipyridine-ligated Ir boryl catalysts. Selectivities can be modulated by both the length of the alkyl groups in the tetraalkylammonium cations and the substituents on the bipyridine ligands. Ion pairing, where the alkyl groups of the cation shield the meta C–H bonds in the counteranions, is proposed to account for para selectivity. The 4,4′-dimethoxy-2,2′-bipyridine ligand gave superior selectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b08464