Metal-free one-pot three-step process for the direct conversion of aryl alkynes into secondary amines with TfOH/B2(OH)4

被引:12
作者
Chen, Yongsheng [1 ]
Liu, Sensheng [1 ]
Cui, Peng [1 ]
Zhang, Yin [1 ]
Liu, Qixing [1 ]
Zhou, Haifeng [1 ]
机构
[1] China Three Gorges Univ, Res Ctr Green Pharmaceut Technol & Proc, Hubei Key Lab Nat Prod Res & Dev, Coll Biol & Pharmaceut Sci, Yichang 443002, Peoples R China
关键词
Diboronic acid; Hydration; Aromatic amines; Reduction; INTERMOLECULAR HYDROAMINATION; CATALYZED HYDRATION; REDUCTIVE HYDROAMINATION; TERMINAL ALKYNES; TRANSITION-METAL; CHIRAL ALCOHOLS; ACID; HYDROGENATIONS; COMPLEXES; SOLVENT;
D O I
10.1016/j.tetlet.2018.12.041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free one-pot synthesis of secondary amines from aryl alkynes via hydration-condensation-reduction three-step process in the presence of TfOH and B-2(OH)(4) has been developed. A series of secondary amines were obtained with good functional group tolerance and satisfied yields. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:327 / 330
页数:4
相关论文
共 38 条
[1]   Simple and efficient AuI-based catalyst for hydroamination of alkynes [J].
Anokhin, Maksim V. ;
Murashkina, Anna V. ;
Averin, Alexei D. ;
Beletskaya, Irina P. .
MENDELEEV COMMUNICATIONS, 2014, 24 (06) :332-333
[2]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[3]   Triazole-Au(I) Complexes: A New Class of Catalysts with Improved Thermal Stability and Reactivity for Intermolecular Alkyne Hydroamination [J].
Duan, Haifeng ;
Sengupta, Sujata ;
Petersen, Jeffrey L. ;
Akhmedov, Novruz G. ;
Shi, Xiaodong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12100-+
[4]   Ligand Effects in the Gold Catalyzed Hydration of Alkynes [J].
Ebule, Rene E. ;
Malhotra, Deepika ;
Hammond, Gerald B. ;
Xu, Bo .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (09) :1478-1481
[5]   Consecutive Intermolecular Reductive Hydroamination: Cooperative Transition-Metal and Chiral Bronsted Acid Catalysis [J].
Fleischer, Steffen ;
Werkmeister, Svenja ;
Zhou, Shaolin ;
Junge, Kathrin ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) :9005-9010
[6]   Efficient Water Reduction with sp3-sp3 Diboron(4) Compounds: Application to Hydrogenations, H-D Exchange Reactions, and Carbonyl Reductions [J].
Flinker, Mathias ;
Yin, Hongfei ;
Juhl, Rene W. ;
Eikeland, Espen Z. ;
Overgaard, Jacob ;
Nielsen, Dennis U. ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (50) :15910-15915
[7]   Alkynes as a versatile platform for construction of chemical molecular complexity and realization of molecular 3D printing [J].
Galkin, K. I. ;
Ananikov, V. P. .
RUSSIAN CHEMICAL REVIEWS, 2016, 85 (03) :226-247
[8]   Solvent-, Silver-, and Acid-Free NHC-Au-X Catalyzed Hydration of Alkynes. The Pivotal Role of the Counterion [J].
Gatto, Mattia ;
Belanzoni, Paola ;
Belpassi, Leonardo ;
Biasiolo, Luca ;
Del Zotto, Alessandro ;
Tarantelli, Francesco ;
Zuccaccia, Daniele .
ACS CATALYSIS, 2016, 6 (11) :7363-7376
[9]   Hydroamination/hydrosilylation sequence catalyzed by titanium complexes [J].
Heutling, A ;
Pohlki, F ;
Bytschkov, I ;
Doye, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (19) :2951-2954
[10]   Late Transition Metal-Catalyzed Hydroamination and Hydroamidation [J].
Huang, Liangbin ;
Arndt, Matthias ;
Goossen, Kaethe ;
Heydt, Heinrich ;
Goossen, Lukas J. .
CHEMICAL REVIEWS, 2015, 115 (07) :2596-2697