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

submitted on 29.10.2019, 22:14 and posted on 31.10.2019, 18:58 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.


NSF 1828573, NSF 0604188, NSF 1352663


Email Address of Submitting Author


Portland State University


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest


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