- Propargylic and allenic carbocycle synthesis through palladium-catalyzed dearomatization reaction
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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(PPh 3)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.
- Peng, Bo,Feng, Xiujuan,Zhang, Xin,Zhang, Sheng,Bao, Ming
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supporting information; experimental part
p. 2619 - 2627
(2010/06/17)
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- Regioselective control using a catalyst switch in the reaction of diarylmethyl chlorides with allyltributylstannane
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Regioselective control in the reaction of diarylmethyl chlorides 5a with allyltributyltin is described. The reaction pathway (allylative dearomatization vs cross-coupling) can be easily controlled using different catalysts. When reactions are performed in
- Peng, Bo,Feng, Xiujuan,Zhang, Xin,Ji, Liyun,Bao, Ming
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supporting information; experimental part
p. 6013 - 6018
(2010/09/18)
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