α-Allenyl Ethers as Starting Materials for Palladium Catalyzed Suzuki-Miyaura Couplings of Allenylphosphine Oxides with Arylboronic Acids.

作者: Yao-Zhong Chen , Ling Zhang , Ai-Min Lu , Fang Yang , Lei Wu

DOI: 10.1021/JO502485U

关键词:

摘要: We disclose here the first palladium-catalyzed Suzuki–Miyaura couplings of aryl ethers functionalized allenylphosphine oxides with arylboronic acids. This new methodology α-allenyl as starting materials provides a novel approach to generate phosphinoyl 1,3-butadienes and derivatives medium excellent yields. The reaction tolerates variety functional groups afford ranges structurally diverse substituted phosphionyl 1,3-butadienes. For unsymmetrical allene substrates, high stereospecific additions give E-isomers are usually observed. On basis known palladium chemistry, mechanism is proposed.

参考文章(80)
Takashi Mino, Taketo Kogure, Taichi Abe, Tomoko Koizumi, Tsutomu Fujita, Masami Sakamoto, Palladium-Catalyzed Allylic Arylation of Allylic Ethers with Arylboronic Acids Using Hydrazone Ligands European Journal of Organic Chemistry. ,vol. 2013, pp. 1501- 1505 ,(2013) , 10.1002/EJOC.201201276
Xiao-Feng Wu, Helfried Neumann, Matthias Beller, Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations Chemical Reviews. ,vol. 113, pp. 1- 35 ,(2013) , 10.1021/CR300100S
Norbert Krause, Christian Winter, Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles. Chemical Reviews. ,vol. 111, pp. 1994- 2009 ,(2011) , 10.1021/CR1004088
Carmen Nájera, Juan Gil-Moltó, Sofia Karlström, Suzuki–Miyaura and Related Cross‐Couplings in Aqueous Solvents Catalyzed by Di(2‐pyridyl)methylamine‐Palladium Dichloride Complexes Advanced Synthesis & Catalysis. ,vol. 346, pp. 1798- 1811 ,(2004) , 10.1002/ADSC.200404195
Hirohisa Ohmiya, Natsumi Yokokawa, Masaya Sawamura, Copper-Catalyzed γ-Selective and Stereospecific Allyl−Aryl Coupling between (Z)-Acyclic and Cyclic Allylic Phosphates and Arylboronates Organic Letters. ,vol. 12, pp. 2438- 2440 ,(2010) , 10.1021/OL100841Y
Ronald Grigg, Stephen Brown, Visuvanathar Sridharan, Michael D Uttley, Intermolecular Heck-Diels-Alder cascade processes of alkylallenes Tetrahedron Letters. ,vol. 39, pp. 3247- 3250 ,(1998) , 10.1016/S0040-4039(98)00403-1
Lei Wu, Xiǎo Zhang, Qing-Qing Chen, An-Kun Zhou, A novel copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides. Organic and Biomolecular Chemistry. ,vol. 10, pp. 7859- 7862 ,(2012) , 10.1039/C2OB26414E
Xin Huang, Xinpeng Jiang, Chunling Fu, Shengming Ma, Palladium(0)‐Catalyzed Regioselective Synthesis of Macrocycles from Allenes with a Nucleophilic Functionality and Organic Iodides Advanced Synthesis & Catalysis. ,vol. 355, pp. 3295- 3303 ,(2013) , 10.1002/ADSC.201300602