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Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

preprint
submitted on 25.10.2019 and posted on 28.10.2019 by Caleb Karmel, Camille Rubel, Elena Kharitonova, John Hartwig
We report that the silylation of five-membered ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of
[Ir(cod)(OMe)]2 and a phenanthroline ligand or a new pyridylimidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C–H bonds of these rings under conditions that the borylation of C–H bonds with previously reported catalysts formed mixtures of products or products that are unstable.

Funding

Discovery and Development of Organic Reactions Catalyzed by Transition Metals Valuable for Medicinal Chemistry

National Institute of General Medical Sciences

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Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, Berkeley

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History

Email Address of Submitting Author

calebkarmel@berkeley.edu

Institution

University of California, Berkeley

Country

USA

ORCID For Submitting Author

0000-0002-1759-6176

Declaration of Conflict of Interest

No conflict of interest

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