- Lewis Acid-Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4-Hydroxy-2H-chromen-2-ones
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A Lewis acid-catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2-c]chromen-5(2H)-one fragments has been developed using propargylic alcohols and 4-hydroxy-2H-chromen-2-on
- Han, Ya-Ping,Li, Xue-Song,Li, Ming,Zhu, Xin-Yu,Liang, Yong-Min
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supporting information
p. 2796 - 2800
(2018/08/17)
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- Cadmium(II) Chloride-Catalyzed Dehydrative C?P Coupling of Propargyl Alcohols with Diarylphosphine Oxides to Afford Allenylphosphine Oxides
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The cadmium(II) chloride-catalyzed dehydrative C?P cross-coupling reaction of propargyl alcohols with diarylphosphine oxides is reported. Several propargyl alcohols including those bearing the sterically demanding tert-butyl group at the triple bond terminus can be used as good substrates in the reaction to produce the corresponding allenylphosphine oxides in good to high yields in acetonitrile at 100 °C. The reaction can also be easily scaled up to a gram-scale synthesis. A mechanism study indicates that the reaction may proceed through a process of propargylic substitution to generate phosphonite intermediates followed by [2,3] sigmatropic rearrangement to produce the allenyl products, rather than through a common allenylative substitution resulting from P-nucleophilicity. (Figure presented.).
- Yang, Jianlin,Zhang, Ming,Qiu, Kang,Wang, Lize,Yu, Jingjing,Xia, Zefeng,Shen, Ruwei,Han, Li-Biao
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supporting information
p. 4417 - 4426
(2017/12/26)
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- Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol
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An unprecedented Lewis acid catalyzed, protection-free, and high-efficiency synthesis of valuable 3,4-dihydro-2H-2,4-methanochromans via cycloaddition of propargylic alkynols with 2-vinylphenol is described. This cycloaddition protocol, which tolerates a
- Han, Ya-Ping,Song, Xian-Rong,Qiu, Yi-Feng,Li, Xue-Song,Zhang, Heng-Rui,Zhu, Xin-Yu,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information
p. 3866 - 3869
(2016/08/16)
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- TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
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A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
- Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
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p. 7616 - 7625
(2014/09/16)
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