La Trobe

Electrophilic activation of molecular bromine mediated by I(III)

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posted on 2025-03-17, 22:52 authored by Lachlan Sharp-Bucknall, Tania TaniaTania Tania, Marcus SceneyMarcus Sceney, Lachlan BarwiseLachlan Barwise, Jason DuttonJason Dutton
In pursuit of a genuine bromo-λ3-iodane, it has been found that the combination of Br2 and electron deficient λ3-iodanes can result in the delivery of both bromine atoms from Br2 to a range of aryl substrates, some highly deactivated. These brominations occur rapidly in common chlorinated solvents at room temperature and can be achieved with the catalytic activation of commercially available PhI(OAc)2 and PhI(OTFA)2. para-NO2 substituted derivatives are employed to direct bromination towards more deactivated substrates. The mechanism of Br2 activation is discussed with insights being made, however it remains unclear.

Funding

La Trobe University and Australian Research Council (FT16010007, DP20010013).

History

Publication Date

2023-11-28

Journal

Dalton Transactions

Volume

52

Issue

44

Pagination

8p. (p. 16472-16479)

Publisher

Royal Society of Chemistry

ISSN

0300-9246

Rights Statement

© The Royal Society of Chemistry 2023. This is the Accepted Version.

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