Gold(I)-Catalyzed Formal Intramolecular Dehydro-Diels-Alder Reaction of Ynamide-ynes: Synthesis of Functionalized Benzo[ b]carbazoles

Organic Letters
Wei XuYuanhong Liu

Abstract

A gold-catalyzed cycloisomerization of ynamide-ynes via a formal dehydro-Diels-Alder reaction has been developed, providing an attractive route to diversely substituted benzo[ b]carbazoles. The reaction likely proceeds via regioselective attack of the pendant alkyne moiety to a keteniminium ion intermediate followed by benzannulation. The method offers several advantages such as high efficiency, mild reaction conditions, and wide functional group tolerance and serves as a highly useful complement to the thermal DDA reactions of ynamide-ynes.

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Citations

Feb 27, 2019·Chemical Communications : Chem Comm·Deng-Yuan LiPei-Nian Liu
Apr 11, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yongjia LinYuanzhi Xia
Mar 5, 2019·Chemistry : a European Journal·Vanessa ClausA Stephen K Hashmi
Feb 19, 2020·Organic & Biomolecular Chemistry·Shuvendu Saha, Modhu Sudan Maji

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