cheminform abstract: copper-catalyzed trifluoromethylation of allylsilanes

1
ChemInform 2012, 43, issue 37 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Halogen compounds Q 0090 DOI: 10.1002/chin.201237050 Copper-Catalyzed Trifluoromethylation of Allylsilanes. — The reaction is per- formed using Togni's reagent (II) and CuI as catalyst. 2-Substituted allylsilanes afford desilylated products, whereas allylsilanes without a substituent in the 2-position give vinylsilane derivatives. An alternative route is found for branched trifluoromethylated alkenes like (V). The treatment of epoxide (X) with alkyllithium compounds provides unexpectedly the desired α-alkylated products in high yields. In addition, the utility of the products is demonstrated by further transformations. — (SHIMIZU, R.; EGAMI, H.; HAMASHIMA, Y.; SODEOKA*, M.; Angew. Chem., Int. Ed. 51 (2012) 19, 4577-4580, http://dx.doi.org/10.1002/anie.201201095 ; RIKEN Adv. Sci. Inst., Wako, Saitama 351-01, Japan; Eng.) — Klein 37- 050

Upload: ryo-shimizu

Post on 12-Oct-2016

212 views

Category:

Documents


0 download

TRANSCRIPT

Halogen compoundsQ 0090 DOI: 10.1002/chin.201237050

Copper-Catalyzed Trifluoromethylation of Allylsilanes. — The reaction is per-formed using Togni's reagent (II) and CuI as catalyst. 2-Substituted allylsilanes afford desilylated products, whereas allylsilanes without a substituent in the 2-position give vinylsilane derivatives. An alternative route is found for branched trifluoromethylated alkenes like (V). The treatment of epoxide (X) with alkyllithium compounds provides unexpectedly the desired α-alkylated products in high yields. In addition, the utility of the products is demonstrated by further transformations. — (SHIMIZU, R.; EGAMI, H.; HAMASHIMA, Y.; SODEOKA*, M.; Angew. Chem., Int. Ed. 51 (2012) 19, 4577-4580, http://dx.doi.org/10.1002/anie.201201095 ; RIKEN Adv. Sci. Inst., Wako, Saitama 351-01, Japan; Eng.) — Klein

37- 050

ChemInform 2012, 43, issue 37 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim