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CSJ Journals

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2020, Vol.49, No.3

264-266

Nickel-catalyzed [4 + 2] Cycloaddition of Styrenes with Arynes via 1:1 Cross-coupling: Synthesis of 9,10-Dihydrophenanthrenes

Teruhiko Kubo ,Takeshi Fujita , and Junji Ichikawa *
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
https://doi.org/10.1246/cl.190906

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Abstract

The [4 + 2] cycloaddition of styrenes with arynes was achieved via 1:1 cross-coupling by a nickel catalyst. This protocol applies to a variety of styrenes and arynes generated in situ from o-(trimethylsilyl)aryl triflates to afford 9,10-dihydrophenanthrenes involving substituted aromatic rings. By using this method, a naturally occurring stilbenoid is easily synthesized.

figure

[4 + 2] Cycloaddition of styrenes with arynes was successfully promoted by a nickel catalyst in a 1:1 ratio to afford 9,10-dihydrophenanthrenes.

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