29866-41-9Relevant academic research and scientific papers
Palladium-Catalyzed C-S Bond Cleavage with Allenoates: Synthesis of Tetrasubstituted 2-Alkenylfuran Derivatives
Wang, Quannan,Liu, Zhuqing,Lou, Jiang,Yu, Zhengkun
supporting information, p. 6007 - 6011 (2018/10/09)
Palladium-catalyzed C-S cleavage of tetrasubstituted internal alkene α-oxo ketene dithioacetals was realized with allenoates as the coupling partners, efficiently affording tetrasubstituted 2-alkenylfuran derivatives with excellent regioselectivity under mild conditions. Allenoates acted as C1 synthons in the desulfurative [4 + 1] annulation.
Controlled Ring-Opening of Siloxydifluorocyclopropanes for Carbocyclization: Synthesis of Difluorocyclopentenones
Song, Xiaoning,Tian, Shuangquan,Zhao, Ziming,Zhu, Dongsheng,Wang, Mang
supporting information, p. 3414 - 3417 (2016/07/26)
A highly controlled ring opening of siloxydifluorocyclopropanes, formed by nBuN4Br-catalyzed difluorocyclopropanation of methyl vinyl ketones bearing a β-alkylthio group by using TMSCF2Br as a unique difluorocarbene source, results in metal difluorohomoenolates with assistance of copper or silver followed by an intramolecular addition and elimination reaction leading to α-gem-difluorocyclopentenones efficiently.
One-pot synthesis of polyfunctionalized 4H-chromenes and dihydrocoumarins based on copper(II) bromide-catalyzed C-C coupling of benzylic alcohols with ketene dithioacetals
Liang, Deqiang,Wang, Mang,Bekturhun, Bahargul,Xiong, Binbin,Liu, Qun
supporting information; experimental part, p. 1593 - 1599 (2010/09/08)
The synthesis of polyfunctionalized 4Hchromenes 3 and dihydrocoumarins 4 has been developed from the same substrates. Catalyzed by copper(II) bromide (0.3 equiv.), the reactions of the easily available ketene dithioacetals 1 with 2-(hydroxymethyl)phenols 2 lead to 4/7-chromenes 3 in high to excellent yields in dichloromethane solvent, whereas, 3,4-trans-disubstituted dihydrocoumarins 4 are obtained in high yields with high diastereoselectivities by prolonging the reaction time or changing the solvent from dichloromethane to acetonitrile.
Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals
Yuan, Hongjuan,Wang, Mang,Liu, Yingjie,Wang, Lili,Liu, Jun,Liu, Qun
experimental part, p. 13450 - 13457 (2011/02/27)
Hydrobromic acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other acids (including Lewis and Bronsted acids), the remarkable catalytic performance of hydrobromic acid in catalytic a
Synthesis of functionalized allylic sulfoxides and their use in the construction of 2,3,4-trisubstituted furans via a [3 + 2] annulation
Fu, Zhenqian,Wang, Mang,Ma, Yuhui,Liu, Qun,Liu, Jun
, p. 7625 - 7630 (2008/12/22)
(Chemical Equation Presented) A route to 2,3,4-trisubstituted furan derivatives based on a [3 + 2] annulation of functionalized allylic sulfoxides and aldehydes is described. In this strategy, the precursors of allylic sulfoxides 4, allylic sulfides 3, were synthesized via a thiomethylation reaction of an α-EWG ketene-S,S-acetal 1 (EWG: electron-withdrawing group), formaldehyde, and a thiol 2 in high to excellent yields. Allylic sulfoxides 4 were prepared by a highly regioselective oxidation of 3, using m-chloroperoxybenzoic acid as oxidant. Thus, starting from these readily available sulfoxides 4, 2-alkylthio-3,4-disubstituted furans 6 were efficiently constructed via the [3 + 2] annulation reaction of 4 with aldehydes 5 under mild conditions. Further replacement of the 2-alkylthio group of 6 with amines led to the formation of 2-amino-3,4-disubstituted furan derivatives 7.
