Journal
ACS CATALYSIS
Volume 8, Issue 2, Pages 920-925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02987
Keywords
C-H iodination; benzoic acids; iridium catalysis; 1,1,1,3,3,3-hexafluoroisopropanol; hydrogen bonding
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Funding
- Swedish Research Council through Vetenskapsradet
- Knut and Alice Wallenberg Foundation
- AstraZeneca
- Generalitat Valenciana (Spain)
- Universitat de Valencia (Spain)
- Wenner-Gren Foundation
- Swedish Research Council through Formas
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A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.
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