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

31 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

hypervalent iodine
aryne
C-H functionalization

Supplementary materials

Title
Description
Actions
Title
Stuart Computational SI
Description
Actions
Title
Stuart Experimental SI
Description
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.