4.5 Article

Highly Efficient Visible-Light-Driven [2+2] Cycloaddition of Maleimides to Alkenes and Alkynes for the Synthesis of 3-Azabicyclo[3.2.0]heptane-Fused Scaffolds

Journal

SYNTHESIS-STUTTGART
Volume 54, Issue 4, Pages 925-942

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1480-3215

Keywords

visible light sensitization; energy transfer; photocatalysis; cycloadditions; 3-azabicyclo[3.2.0]heptanes

Funding

  1. National Natural Science Foundation of China [21871123]

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A highly efficient [2+2] cycloaddition between maleimides and unsaturated moieties has been developed utilizing a visible-light triplet sensitization mode for the direct synthesis of multifunctional 3-azabicyclo[3.2.0]heptane derivatives. This strategy overcomes previous obstacles such as limited substrate scope and undesired reaction pathways under harsh UV irradiation by selectively activating the maleimide functionality through energy transfer from a new photosensitizer.
A highly efficient [2+2] cycloaddition between maleimides and unsaturated moieties, utilizing a visible-light triplet sensitization mode, has been developed for the direct synthesis of multifunctional 3-azabicyclo[3.2.0]heptane derivatives. This reaction relies on selective activation of the maleimide functionality upon energy transfer from a new photosensitizer that outperforms diverse well-established photosensitizers. The strategy developed herein overcomes previous obstacles such as limited substrate scope and undesired reaction pathways under harsh UV irradiation.

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