Synthesis, Structure, and Reactivity of Hypervalent Iodine Reagents Stabilized by Internal Out-of-Plane Halogen Bonding: ortho-Bromo and ortho-Chloro-Substituted [Hydroxy(tosyloxy)iodo]arenes and Iodonium Ylides.

Authors

Niloofar Zarrabi, Grayson Hughes, Brianna Herrmann, Simon Krystosek, Daniel R Tyson, Yoshi Funk, Gregory T Rohde, Viktor V Zhdankin

Published in

The Journal of organic chemistry. Jun 21, 2026. Epub Jun 21, 2026.

Abstract

The preparation and reactivity of a series of ortho-halogen-substituted (diacetoxyiodo)arenes, [hydroxy(tosyloxy)iodo]arenes, and aryliodonium ylides are reported. X-ray analysis of 1-[hydroxy(tosyloxy)iodo]-2-bromobenzene confirms the presence of halogen bonds in the intramolecular interactions between the ortho-halogen atom and the hypervalent iodine center, with a normalized contact (observed contact length divided by the sum of the van der Waals radii) value of 0.91. The o-bromo-substituted aryliodonium ylide can be handled and stored at room temperature and can serve as a convenient carbene precursor in a Rh-catalyzed cyclopropanation reaction with styrenes, affording the corresponding cyclopropane products in 59-75% yields.

PMID:
42324680
Bibliographic data and abstract were imported from PubMed on 22 Jun 2026.

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