A Cascade Suzuki–Miyaura/Diels–Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin
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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 postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels–Alder process was also assessed.
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1963 ◽
Vol 4
(19)
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pp. 1243-1245
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2007 ◽
Vol 79
(4)
◽
pp. 651-665
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