A cascade Suzuki-Miyaura/Diels-Alder protocol : exploring the bifunctional utility of vinyl Bpin
Abstract
Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.
Citation
Cain , D L , McLaughlin , C , Molloy , J , Carpenter-Warren , C , Anderson , N A & Watson , A J B 2019 , ' A cascade Suzuki-Miyaura/Diels-Alder protocol : exploring the bifunctional utility of vinyl Bpin ' , Synlett , vol. 30 , no. 7 , pp. 787-791 . https://doi.org/10.1055/s-0037-1611228
Publication
Synlett
Status
Peer reviewed
ISSN
0936-5214Type
Journal article
Description
Funding: Industrial CASE studentship awarded from EPSRC and GlaxoSmithKline. The authors thank the EPSRC, GlaxoSmithKline, and the University of St Andrews for studentship funding (DLC), and the University of St Andrews and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.Collections
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