4.8 Article

Rhodium-Catalyzed Dehydrogenative Cycloisomerization of Dienylcyclopropane to Highly Substituted Toluene

Journal

ORGANIC LETTERS
Volume 23, Issue 11, Pages 4337-4341

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01265

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Funding

  1. National Natural Science Foundation of China [21572199]

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A rhodium-catalyzed dehydrogenative cycloisomerization of dienylcyclopropane compounds is reported, providing a straightforward approach to highly substituted toluene derivatives in yields of 67-85%. The dienylcyclopropaneimides are produced through a single-step olefination procedure. Preliminary mechanistic studies suggest that an electron-withdrawing group as R is crucial for completing this transformation.
A rhodium-catalyzed dehydrogenative cycloisomerization of dienylcyclopropane compounds is reported, which provides a straightforward approach to a variety of highly substituted toluene derivatives in 67-85% yields. The dienylcyclopropaneimides are produced by a single-step formal three-component olefination procedure. Preliminary mechanistic studies indicated that an electron-withdrawing group as R plays a critical role in completing this transformation.

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