Construction of Bridged Carbocycles and Heterocycles via Rh(III)-Catalyzed C-H Alkylation/Michael Addition of 2-Arylindoles with Quinone Monoacetals.

The Journal of Organic Chemistry
Shenghai GuoXuesen Fan

Abstract

A rhodium-catalyzed formal [4 + 5] annulation reaction of 2-arylindoles with quinone monoacetals for the selective preparation of bridged nine-membered carbocyclic and heterocyclic compounds is developed. When 2-aryl substituted indoles are employed, this annulation reaction affords bridged nine-membered carbocyclic compounds with excellent indolyl C3 selectivity. On the other hand, with 2-aryl-3-substituted indoles as the substrates, bridged nine-membered heterocyclic compounds are exclusively formed via N1 annulation. Further transformations of the obtained products into new bridged compounds showcase the synthetic potential of this protocol.

References

Apr 3, 2003·Journal of the American Chemical Society·Yahua Liu, William W McWhorter
Apr 7, 2015·Accounts of Chemical Research·Guoyong Song, Xingwei Li

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