- Gold-catalyzed tandem annulations of pyridylhomopropargylic alcohols with propargyl alcohols
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A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols is achieved, providing an atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer?Schuster rearrangement/Friedel?Crafts-type pathway. In this way, three C?C bonds and one C? O bond form to give a polycyclic skeleton in a one-pot process. Moreover, the products exhibit unique optical properties, which reveal their potential application value.
- Li, Xue-Song,Xu, Dan-Tong,Niu, Zhi-Jie,Li, Ming,Shi, Wei-Yu,Wang, Cui-Tian,Wei, Wan-Xu,Liang, Yong-Min
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supporting information
p. 832 - 836
(2021/02/16)
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- Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols
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A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer–Schuster rearrangement, ring expansion, and Friedel–Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.
- Kong, Xiangtao,Li, Xue-Song,Li, Yuke,Liang, Yong-Min,Liu, Hong-Chao,Niu, Zhi-Jie,Wang, Cui-Tian,Wei, Wan-Xu,Zhang, Zhe
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supporting information
p. 9457 - 9462
(2021/12/14)
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- Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
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A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
- Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
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supporting information
(2020/03/04)
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- Br?nsted Acid-Mediated Formal [3+3] Annulation Between Propargylic Alcohols and 1,3-Diketones
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A Br?nsted acid-mediated formal [3+3] cascade annulation of propargylic alcohols with 1,3-diketones proceeds through a sequential Meyer?Schuster rearrangement/1,2-addition. This protocol, which has a wide scope and is conducted under an ambient atmosphere
- Han, Ya-Ping,Li, Xue-Song,Zhu, Xin-Yu,Sun, Zhou,Li, Ming,Wang, Yu-Zhao,Liang, Yong-Min
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supporting information
p. 870 - 874
(2017/12/26)
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- 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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- Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (Z)-2-Styryl-1H-Indoles
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A novel copper(II) trifluoromethanesulfonate-catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)-2-styryl-1H-indoles as the initial substrates. This protocol, which entails a sequential Meyer-Schuster rearrangement/isomerization/-cyclization cascade, enables facile and atom-economical access to various pentacyclic compounds with broad functional-group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work. (Figure presented.).
- Li, Xue-Song,Han, Ya-Ping,Zhu, Xin-Yu,Xia, Yu,Wei, Wan-Xu,Li, Ming,Liang, Yong-Min
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supporting information
p. 4441 - 4445
(2018/10/15)
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- Lewis Acid-Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[d]isoxazoles
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An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d]isoxazoles proceeds through a sequential ring opening/Meyer–Schuster rearrangement/intermolecular cyclization. This protocol, whi
- Han, Ya-Ping,Li, Xue-Song,Sun, Zhou,Zhu, Xin-Yu,Li, Ming,Song, Xian-Rong,Liang, Yong-Min
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supporting information
p. 2735 - 2740
(2017/08/23)
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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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- Lewis acid mediated tandem reaction of propargylic alcohols to tetrazoles involving C-O- and C-C-bond cleavage reactions and a C-N-bond formation
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A novel and direct synthesis of 1-aryl-5-arylvinyl-tetrazoles from easily prepared propargylic alcohols and TMSN3 is developed in the presence of TMSCl under mild conditions (TMS=trimethylsilyl). The process involves an allenylazide intermediate, followed by a C-C-bond cleavage and C-N-bond formation to afford the desired products. Moreover, this method offers a good functional-group applicability and can be scaled-up to grams (yield up to 85%).
- Song, Xian-Rong,Han, Ya-Ping,Qiu, Yi-Feng,Qiu, Zi-Hang,Liu, Xue-Yuan,Xu, Peng-Fei,Liang, Yong-Min
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supporting information
p. 12046 - 12050
(2015/03/31)
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- Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides
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An efficient synthetic method to prepare di- and trisubstituted 2-aryloxazoles based on Yb(OTf)3 catalyzed cyclization of trisubstituted propargylic alcohols with aryl amides is described. The reaction was accomplished in moderate to excellent product yields and with complete regioselective control. The mechanism is suggested to involve activation of the starting alcohol by the metal catalyst that results in its ionization. Subsequent cyclization of this newly generated carbocationic species with the aryl amide then affords the oxazole. In view of the mild conditions along with the low cost, commercially availability of Yb(OTf)3 and its high tolerance to air and moisture, the present synthetic approach offers an operationally simplistic and convenient route to this important aromatic heterocycle.
- Zhang, Xiaoxiang,Teo, Wan Teng,Chan, Philip Wai Hong
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supporting information; experimental part
p. 331 - 337
(2011/02/17)
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- Bronsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of Di- and trisubstituted thiazoles
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Figure presented. A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.
- Zhang, Xiaoxiang,Teo, Wan Teng,Sally,Chan, Philip Wai Hong
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supporting information; experimental part
p. 6290 - 6293
(2010/11/18)
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- Ytterbium(III) triflate catalyzed tandem friedel-crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols
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A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel - Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished In moderate to excellent yields and regioselectivity under mild conditions and offers a straightforward and convenient one step synthetic route to bioactive indenols and its derivatives.
- Zhang, Xiaoxiang,Teo, Wan Teng,Chan, Philip Wai Hong
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supporting information; experimental part
p. 4990 - 4993
(2009/12/28)
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