Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd-Catalyzed Allylation Reaction

作者: Kazuyuki Sato , Yu Takiguchi , Yosuke Yoshizawa , Kayoko Iwase , Yoshie Shimizu

DOI: 10.1248/CPB.55.1593

关键词: FluorineGroup (periodic table)Palladium catalystOrganic chemistryChemical synthesisChemistryCarbonTrifluoromethylQuaternary carbonCatalysis

摘要: Synthesis of compounds with quaternary carbons is one the most attractive reactions in synthetic chemistry. However, there are only a few reports on synthesis fluoroalkyl group at carbon center. Recently, we reported α-trifluoromethylated ketones by reaction α,β-unsaturated CF3-I using Rh catalyst. When and allyl carbonates were treated Pd catalyst, allylation proceeded smoothly trifluoromethylated to give desired center good excellent yields.

参考文章(15)
John T. Welch, Tetrahedron report number 221 Tetrahedron. ,vol. 43, pp. 3123- 3197 ,(1987) , 10.1016/S0040-4020(01)90286-8
Kazuyuki Sato, Masaaki Omote, Akira Ando, Itsumaro Kumadaki, Trifluoromethylation at the α‐Position of α,β‐Unsaturated Ketones: 4‐Phenyl‐3‐(Trifluoromethyl)Butan‐2‐One Organic Syntheses. ,vol. 83, pp. 177- 183 ,(2006) , 10.1002/0471264229.OS083.23
Nobuo Ishikawa, Tsutomu Yokozawa, Convenient Preparation of Dimethyl (Trifluoromethyl)malonate and Related Compounds Bulletin of the Chemical Society of Japan. ,vol. 56, pp. 724- 726 ,(1983) , 10.1246/BCSJ.56.724
Mitsuo Kimura, Takashi Yamazaki, Tomoya Kitazume, Toshio Kubota, Construction of Optically Active CF3-Containing Quaternary Carbon Centers via Stereospecific SN2‘ Reaction† Organic Letters. ,vol. 6, pp. 4651- 4654 ,(2004) , 10.1021/OL0481941
Tsutomu Konno, Masashi Kanda, Takashi Ishihara, Hiroki Yamanaka, A novel synthesis of fluorine-containing quaternary amino acid derivatives via palladium-catalyzed allylation reaction Journal of Fluorine Chemistry. ,vol. 126, pp. 1517- 1523 ,(2005) , 10.1016/J.JFLUCHEM.2005.08.013
Yuzo Komatsu, Toru Sakamoto, Tomoya Kitazume, Synthetic Applications of the Carbanion with a Fluoroalkyl Group Generated by Palladium(0) Catalyst under Neutral Conditions. Journal of Organic Chemistry. ,vol. 64, pp. 8369- 8374 ,(1999) , 10.1021/JO990463R
Matthew J. Tozer, Timothée F. Herpin, Methods for the synthesis of gem-difluoromethylene compounds Tetrahedron. ,vol. 52, pp. 8619- 8683 ,(1996) , 10.1016/0040-4020(96)00311-0