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September 14, 2026Organic Letters

Aminohalogenation of Alkenes Enabled by I(I)/I(III) Catalysis

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Authors

QYQuan YinKDKong De-yiFGFan Gong

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Overview

Laboratory study demonstrates catalytic aminohalogenation across diverse alkenes via an iodine cycle, highlighting divergent regioselectivity for chemical synthesis.

Key Points

  • Develop a unified, mild catalytic protocol for the aminohalogenation of diverse alkenes utilizing an I(I)/I(III) catalytic cycle.
  • Applied an iodoarene catalyst in the presence of inexpensive halogen sources to install chlorine, bromine, or iodine across diverse alkenes at room temperature.
  • Conducted mechanistic experiments to elucidate the underlying pathway and characterize the active reaction intermediates.
  • Achieved broad and unified room-temperature installation of Cl, Br, and I across both aryl- and alkyl-substituted alkenes.
  • Identified divergent regioselectivity governed by electronic and steric factors, providing Markovnikov products for aryl alkenes and sterically controlled attack for alkyl alkenes.
  • Established that the reaction proceeds via an electrophilic mechanism involving a reactive hypervalent imidoiodine intermediate.

Cite This Study

Yin et al. (2026) studied this question.

synapsesocial.com/papers/6aa7b3950926e14a848b29e0https://doi.org/10.1021/acs.orglett.6c03347
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