Microwave assisted copper triflate-catalyzed rapid hydration of aryl acetylenes

被引:14
作者
Jha, Mukund [1 ]
Shelke, Ganesh M. [1 ,2 ]
Pericherla, Kasiviswanadharaju [2 ]
Kumar, Anil [2 ]
机构
[1] Nipissing Univ, Dept Biol & Chem, North Bay, ON P1B 8L7, Canada
[2] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
基金
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词
Aryl acetylene; Hydration; Acetophenone; Microwave-assisted; Rare earth metal triflates; Copper triflate; ANTI-MARKOVNIKOV HYDRATION; TERMINAL ALKYNES; GOLD(I) COMPLEXES; REGIOSELECTIVE HYDRATION; ROOM-TEMPERATURE; KETONES; WATER; ACID; ALDEHYDES; CHLORIDE;
D O I
10.1016/j.tetlet.2014.06.116
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient microwave-assisted copper triflate-catalyzed reaction for the hydration of terminal aryl acetylenes to prepare substituted acetophenones has been developed. Significantly shorter reaction time, low catalyst loading, and wide range of functional group tolerance are salient features of this methodology. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4814 / 4816
页数:3
相关论文
共 59 条
[1]   Novel Sulfonated N-Heterocyclic Carbene Gold(I) Complexes: Homogeneous Gold Catalysis for the Hydration of Terminal Alkynes in Aqueous Media [J].
Almassy, Ambroz ;
Nagy, Csilla E. ;
Benyei, Attila C. ;
Joo, Ferenc .
ORGANOMETALLICS, 2010, 29 (11) :2484-2490
[2]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[3]   Hydration of alkynes by a PtCl4-CO catalyst [J].
Baidossi, W ;
Lahav, M ;
Blum, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :669-672
[4]  
Bechara WS, 2012, NAT CHEM, V4, P228, DOI [10.1038/nchem.1268, 10.1038/NCHEM.1268]
[5]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[6]   ALKYNE HYDRATION PROMOTED BY RHCL3 AND QUATERNARY AMMONIUM-SALTS [J].
BLUM, J ;
HUMINER, H ;
ALPER, H .
JOURNAL OF MOLECULAR CATALYSIS, 1992, 75 (02) :153-160
[7]   Mixed Phosphane η5-CpRuCl(PR3)2 Complexes as Ambifunctional Catalysts for Anti-Markovnikov Hydration of Terminal Alkynes [J].
Boeck, Florian ;
Kribber, Thomas ;
Xiao, Li ;
Hintermann, Lukas .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8138-8141
[8]   Gold in Total Synthesis: Alkynes as Carbonyl Surrogates [J].
Brenzovich, William E., Jr. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :8933-8935
[10]   Regioselective Hydration of Alkynes by Iron(III) Lewis/Bronsted Catalysis [J].
Cabrero-Antonino, Jose R. ;
Leyva-Perez, Antonio ;
Corma, Avelino .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (35) :11107-11114