Ammonia borane as a reducing agent in organic synthesis

被引:52
作者
Faverio, Chiara [1 ]
Boselli, Monica Fiorenza [1 ]
Medici, Fabrizio [1 ]
Benaglia, Maurizio [1 ]
机构
[1] Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy
关键词
FRUSTRATED LEWIS PAIRS; ASYMMETRIC TRANSFER HYDROGENATIONS; AMINE-BORANES; PHOSPHORUS-COMPOUND; PINCER COMPLEX; ONE-POT; REDUCTION; ALDEHYDES; KETONES; MILD;
D O I
10.1039/d0ob01351j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ammonia borane NH3 center dot BH(3)is considered a promising material for hydrogen storage and release, and is attracting increasing attention as a relatively inexpensive, atom economy-convenient and viable reagent for developing new green synthetic transformations. The present review offers a wide overview on the use of AB in the reduction of organic compounds, and highlights the versatility of this reagent, due to the possibility of modulating its activity employing different strategies, which include the use of transition metals, p-block species, organocatalysts and FLP systems.
引用
收藏
页码:7789 / 7813
页数:25
相关论文
共 92 条
[81]   Transfer Hydrogenation of Imines with Ammonia-Borane: A Concerted Double-Hydrogen-Transfer Reaction [J].
Yang, Xianghua ;
Zhao, Lili ;
Fox, Thomas ;
Wang, Zhi-Xiang ;
Berke, Heinz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) :2058-2062
[82]   Theoretical Study of Hydrogenation Catalysis of Phosphorus Compound and Prediction of Catalyst with High Activity and Wide Application Scope [J].
Zeng, Guixiang ;
Maeda, Satoshi ;
Taketsugu, Tetsuya ;
Sakaki, Shigeyoshi .
ACS CATALYSIS, 2016, 6 (08) :4859-4870
[83]   Catalytic Transfer Hydrogenation by a Trivalent Phosphorus Compound: Phosphorus- Ligand Cooperation Pathway or PIII/ PV Redox Pathway? [J].
Zeng, Guixiang ;
Maeda, Satoshi ;
Taketsugu, Tetsuya ;
Sakaki, Shigeyoshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (18) :4633-4637
[84]   Lewis Base Promoted Reduction of CO2 with BH3NH3 into Boryl Formates: CO2 as a Carbon Source in Organic Synthesis Under Mild Conditions [J].
Zhang, Bo ;
Du, Gaixia ;
Hang, Wei ;
Wang, Sheng ;
Xi, Chanjuan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (14) :1739-1743
[85]   Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes [J].
Zhang, Sheng ;
Bedi, Deepika ;
Cheng, Lu ;
Unruh, Daniel K. ;
Li, Guigen ;
Findlater, Michael .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (19) :8910-8917
[86]   Catalyst-free N-formylation of amines using BH3NH3 and CO2 under mild conditions [J].
Zhao, Tian-Xiang ;
Zhai, Gao-Wen ;
Liang, Jian ;
Li, Ping ;
Hu, Xing-Bang ;
Wu, You-Ting .
CHEMICAL COMMUNICATIONS, 2017, 53 (57) :8046-8049
[87]   Asymmetric transfer hydrogenations of β-N-substituted enamino esters with ammonia borane [J].
Zhao, Weiwei ;
Feng, Xiangqing ;
Yang, Jing ;
Du, Haifeng .
TETRAHEDRON LETTERS, 2019, 60 (17) :1193-1196
[88]   Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane [J].
Zhou, Qiwen ;
Meng, Wei ;
Feng, Xiangqing ;
Du, Haifeng ;
Yang, Jing .
TETRAHEDRON LETTERS, 2020, 61 (03)
[89]   A Continuously Regenerable Chiral Ammonia Borane for Asymmetric Transfer Hydrogenations [J].
Zhou, Qiwen ;
Meng, Wei ;
Yang, Jing ;
Du, Haifeng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12111-12115
[90]   Borane-Catalyzed Transfer Hydrogenations of Pyridines with Ammonia Borane [J].
Zhou, Qiwen ;
Zhang, Lanqiong ;
Meng, Wei ;
Feng, Xiangqing ;
Yang, Jing ;
Du, Haifeng .
ORGANIC LETTERS, 2016, 18 (20) :5189-5191