Journal
ORGANIC LETTERS
Volume 21, Issue 4, Pages 1152-1155Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00099
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Funding
- National Natural Science Foundation of China (NSFC) [21502123, 21432005]
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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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