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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Iron-Catalyzed Divergent Borylation of α-Aryl-Substituted Allylic Alcohols
Xu-Ya Ma1, Hai-Yue Zhou1, Xiao-Dan Zhang1
1School of Science, Hebei Provincial Key Laboratory of Photoelectric Control on Surface and Interface, Hebei University of Science and Technology, Shijiazhuang 050022, China.
Abstract:
Herein, an iron-catalyzed divergent borylation of α-aryl-substituted allylic alcohols is reported. Precise tuning of the reaction system enables control over the chemo-, regio-, and stereoselectivities, providing divergent access to three valuable classes of organoboron compounds: β-borylated alkylarenes, γ-borylated alkylarenes, and allylic boronates. Mechanistic studies reveal that β-borylated alkylarenes are formed via a sequential hydrodeoxygenation-olefin isomerization-hydroboration cascade, γ-borylated alkylarenes are produced through hydrodeoxygenation followed by selective hydroboration of β,γ-olefin intermediates, and allylic boronates are generated via a mechanism featuring a six-membered cyclic transition state.
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