Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control

Peng-Bo Bai, Alastair Durie, Gang-Wei Wang () and Igor Larrosa ()
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Peng-Bo Bai: Lanzhou University
Alastair Durie: University of Manchester
Gang-Wei Wang: Lanzhou University
Igor Larrosa: University of Manchester

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities.

Date: 2024
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DOI: 10.1038/s41467-023-44219-6

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