Issue 50, 2023

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.

Graphical abstract: Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2] cycloaddition

Supplementary files

Article information

Article type
Communication
Submitted
17 feb 2023
Accepted
26 mei 2023
First published
26 mei 2023
This article is Open Access
Creative Commons BY license

Chem. Commun., 2023,59, 7759-7762

Synthesis of complex aryl MIDA boronates by Rh-catalyzed [2+2+2] cycloaddition

J. M. Halford-McGuff, D. B. Cordes and A. J. B. Watson, Chem. Commun., 2023, 59, 7759 DOI: 10.1039/D3CC00761H

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