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Article Dans Une Revue Angewandte Chemie International Edition Année : 2024

Cyclic Diaryl λ 3 ‐Bromanes as a Precursor for Regiodivergent Alkynylation Reactions

Maxime de Abreu
  • Fonction : Auteur
Torben Rogge
  • Fonction : Auteur
Kendall N. Houk
  • Fonction : Auteur

Résumé

Regiodivergent reactions are a fascinating tool to rapidly access molecular diversity while using identical coupling partners. We have developed a new approach for regiodivergent synthesis using the dual character of hypervalent bromines. In addition to the recently reported reactivity of hypervalent bromines as aryne precursors, the first transition metal-catalyzed reaction is reported. Accordingly, the development of these two complementary transformations allows for the alteration of regioselectivity to furnish both ortho- and meta-substituted alkynylation products. Mechanistic and computational studies show how these selectivities are controlled.

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hal-04568161 , version 1 (03-05-2024)

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Maxime de Abreu, Torben Rogge, Matteo Lanzi, Tomas J. Saiegh, Kendall N. Houk, et al.. Cyclic Diaryl λ 3 ‐Bromanes as a Precursor for Regiodivergent Alkynylation Reactions. Angewandte Chemie International Edition, 2024, 63 (16), ⟨10.1002/anie.202319960⟩. ⟨hal-04568161⟩
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