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Highly Chemo-, Regio- and E/Z-Selective Intermolecular Heck-Type Dearomative [2 + 2 + 1] Spiroannulation of Alkyl
Xingrong Liao1, Deping Wang1, Yueyuan Huang1
1Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry , Sichuan University , 29 Wangjiang Road , Chengdu 610064 , P.R. China.
Abstract:
Described herein is a palladium-catalyzed dearomative annulation of alkyl bromoarenes with internal alkynes. Challenges in this spiroannulation include the chemoselectivity among [2 + 2 + 1], [2 + 2 + 2], and [3 + 2] annulations and the E/ Z-selectivity associated with the generated exocyclic double bond. In the presence of Pd(OAc)2 and a phosphine ligand, a variety of highly functionalized spirocyclopentadienes with an exocyclic carbon-carbon double bond are provided in good to excellent yields with high chemo-, regio-, and E/ Z-selectivity via a Heck-type pathway.
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