Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction
journal contributionposted on 16.04.2010, 00:00 by Bo Peng, Xiujuan Feng, Xin Zhang, Sheng Zhang, Ming Bao
Any type of content formally published in an academic journal, usually following a peer-review process.
The dearomatization reaction of benzylic chlorides (1a−k), chloromethylnaphthalenes (1l−r), and naphthalene allyl chlorides (3a−d) 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 1a−k proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1l−k and 3a−d. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.