Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2] cycloaddition
Abstract
A Rh-catalyzed [2+2+2] cycloaddition approach for the synthesis of BMIDA-functionalized arenes is reported. The developed method overcomes the long-standing reactivity problems associated with internal alkynes and allows access to highly functionalized borylated benzene scaffolds. The method is broadly functional group tolerant and generally high yielding. The utility of the products is demonstrated through elaboration of the BMIDA motif, and in the synthesis of fused heterocycles via intramolecular Chan–Lam etherification and amination. The dominance of sterically controlled reactivity is described.
Citation
Halford-McGuff , J M , Cordes , D B & Watson , A J B 2023 , ' Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2] cycloaddition ' , Chemical Communications , vol. 59 , no. 50 , pp. 7759-7762 . https://doi.org/10.1039/d3cc00761h
Publication
Chemical Communications
Status
Peer reviewed
ISSN
1359-7345Type
Journal article
Description
Funding: J. M. H.-M. thanks the EPSRC Centre for Doctoral Training EaSI-CAT for a PhD studentship. A. J. B. W. thanks the Leverhulme Trust for a Research Fellowship (RF-2022-014) and the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support.Collections
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