Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

• Shuhei Sumino,
• Takahide Fukuyama,
• Mika Sasano,
• Ilhyong Ryu,
• Antoine Jacquet,
• Frédéric Robert and
• Yannick Landais

Beilstein J. Org. Chem. 2019, 15, 1822–1828, doi:10.3762/bjoc.15.176

• , Institute of Molecular Sciences, UMR-CNRS 5255, 351 cours de la libération, Talence, 33405 Cedex, France 10.3762/bjoc.15.176 Abstract Four-component coupling reactions between xanthogenates, alkenes, CO, and sulfonyl oxime ethers were studied. In the presence of hexabutylditin, working as a propagating

• functionalities, have the potential for further elaboration. Keywords: CO; multicomponent reaction; radicals; sulfonyl oxime ethers; xanthogenates; Introduction Multicomponent reactions constitute a powerful and highly efficient tool in organic synthesis to build up intricate compounds from simple molecules in

• reaction using xanthogenates, alkenes, and sulfonyl oxime ethers (Scheme 1, reaction 1) [21][22]. The reaction proceeds efficiently to provide good yields of α-alkoxyimino esters, potential precursors of lactams, lactones and β-keto esters. Since the three-component radical reaction involving alkyl halides

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• desulfurization-fluorination has been disclosed by Hiyama [24][25][26][27]. When dithiocarbonates (2, xanthogenates) are exposed to a huge excess of hydrogen fluoride-pyridine and 1,3-dibromo-5,5-dimethylhydantoin, trifluoromethyl ethers form in moderate to excellent yields (Scheme 5 and Table 5). What makes this