Borylated Cyclohexenes via Cascade Suzuki–Miyaura/Diels–Alder Reaction

A Cascade Suzuki–Miyaura/Diels–Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin: D. L. Cain, C. McLaughlin, J. J. Molloy, C. Carpenter-Warren, N. A. Anderson, Allan J. B. Watson
Synlett 2018, DOI: 10.1055/s-0037-1611228

Cascade and tandem reactions are extremely useful for minimizing work-up and purification procedures, allowing at the same time an improvement of chemical efficiency, especially by simplifying the use of highly reactive and unstable intermediates. Professor Allan J. B. Watson and co-workers from the University of St Andrews (UK) recently described a novel Suzuki–Miyaura/Diels–Alder cascade process. The reaction makes use of a vinyl-borylated derivative as a bifunctional reagent, which first gives a cross-coupling with a vinyl bromide or triflate and then acts as a dienophile with the resulting intermediate diene affording the corresponding borylated cyclohexenes, which can be oxidized to the carbinol end products.

Professor Watson said: “We believe this approach will be useful for the preparation of novel borylated scaffolds for organic synthesis.”
Get Trial Access to the chemistry journals
Download SYNFORM or read it online