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Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction

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journal contribution
posted on 16.04.2010, 00:00 by Bo Peng, Xiujuan Feng, Xin Zhang, Sheng Zhang, Ming Bao
The dearomatization reaction of benzylic chlorides (1ak), chloromethylnaphthalenes (1lr), and naphthalene allyl chlorides (3ad) with allenyltributyltin proceeded smoothly in the presence of Pd(PPh3)4 catalyst at room temperature to give the corresponding propargylated and/or allenylated dearomatization products (5, 5′; 6, 6′; and 7, respectively) in high to fair yields. The reaction of 1ak proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1lk and 3ad. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.