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Updated: May 10, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis
Shu-Sheng Chen1, Yu Zheng1, Zhi-Xi Xing1
1School of Physical Science and Technology, ShanghaiTech University, Shanghai, China.
Abstract:
Borylated carbocycles occupy a pivotal position as essential components in synthetic chemistry, drug discovery, and materials science. Herein, we present a photorearrangement that uniquely involves a boron atom enabled by energy transfer catalysis under visible light conditions. The boron functional group could be translocated through energy transfer mechanism and valuable borylated cyclopropane scaffolds could be generated smoothly. Furthermore, we showcase a 1,5-HAT (hydrogen atom transfer)/cyclization reaction, which is also enhanced by energy transfer catalysis excited by visible light. This method enables the synthesis of borylated cyclobutane frameworks. These boron-involved photorearrangement and cyclization reactions represent two techniques for synthesizing highly desirable borylated strained ring structures, which offering avenues for the synthesis of complex organic molecules with medicinal and material science applications.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

