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Iodane-Guided C-H Cleavage to Synthesize Densely Functionalized Arenes

preprint
submitted on 29.10.2019 and posted on 31.10.2019 by Aleksandra Nilova, Paul A. Sibbald, Edward. J. Valente, Gisela Gonzalez-Monteil, H. Camille Richardson, Kevin S. Brown, Paul Cheong, David Stuart
We describe a strategy for the iodane-guided functionalization of sterically congested C-H bonds, which is distinct from electronic, steric or proximity guided C-H functionalization methods. Readily accessible aryl(Mes)iodonium salts serve as the starting materials in these reactions and produce complex 1,2,3,4-substituted arenes via aryne intermediates. This approach is especially powerful when coupled with the innate C-H functionalization reactivity of simple arenes, to replace two C-H bonds with two C-C or C-heteroatom bonds while over-riding steric effects that typically inhibit such reactions. DFT stud-ies reveal a contribution of inductive, resonance, and steric effects on the regioselectivity of C-H cleavage and aryne generatation.

Funding

NSF 1828573, NSF 0604188, NSF 1352663

History

Email Address of Submitting Author

dstuart@pdx.edu

Institution

Portland State University

Country

United States

ORCID For Submitting Author

0000-0003-3519-9067

Declaration of Conflict of Interest

No conflict of interest

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