Journal
ORGANIC LETTERS
Volume 14, Issue 13, Pages 3558-3561Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301635x
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Funding
- American Chemical Society Petroleum Research Fund [47598-GB3]
- Cambridge Isotope Laboratories, Inc.
- Research Corporation for Science Advancement
- M. J. Murdock Charitable Trust
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The iridium-catalyzed arene C-H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4'-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.
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