Visible Light-Promoted Construction of Cage-Like Frameworks by Sequential [2 + 2] Cycloaddition
Zhuhai Zhang1, Yu Feng1, Jianfu Chen2
1School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China.
Abstract:
A sequential [2 + 2] cycloaddition of unsaturated N-acylindoles was developed under visible light irradiation in the presence of a photosensitizer, forming unprecedented cage-like medium-ring frameworks in high yields. By exploiting the distinct reactivity and selectivity of two types of olefins within the substrate, the transformation provides a single-step and atom-economical approach to such molecules with exclusive regio- and diastereoselectivity, excellent functional group tolerance, and mild reaction conditions. Experimental mechanistic and calculation studies suggest that this reaction proceeds through an energy transfer pathway in this double [2 + 2] cycloaddition process.
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