Iron-Catalyzed 1,2-Selective Hydroboration of N-Heteroarenes

被引:96
作者
Zhang, Fanjun [1 ]
Song, Heng [1 ]
Zhuang, Xuewen [1 ]
Tung, Chen-Ho [1 ]
Wang, Wenguang [1 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, 27 South Shanda Rd, Jinan 250100, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND ACTIVATION; BIOMIMETIC ASYMMETRIC HYDROGENATION; REGIOSELECTIVE 1,4-HYDROBORATION; ORGANIC-SYNTHESIS; HYDRIDE TRANSFER; HANTZSCH ESTERS; PINCER COMPLEX; PYRIDINES; HYDROSILYLATION; DINITROGEN;
D O I
10.1021/jacs.7b11416
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A N-2-bridged diiron complex [Cp*-(Ph2PC6H4S)Fe](2)(mu-N-2) (1) has been found to catalyze the hydroboration of N-heteroarenes with pinacolborane, giving N-borylated 1,2-reduced products with high regioselectivity. The catalysis is initiated by coordination of N-heteroarenes to the iron center, while the B-H bond cleavage is the rate-determining step.
引用
收藏
页码:17775 / 17778
页数:4
相关论文
共 64 条
[1]   Magnesium Catalysis of Imine Hydroboration [J].
Arrowsmith, Merle ;
Hill, Michael S. ;
Kociok-Koehn, Gabriele .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (08) :2776-2783
[2]   Magnesium-Catalyzed Hydroboration of Pyridines [J].
Arrowsmith, Merle ;
Hill, Michael S. ;
Hadlington, Terrance ;
Kociok-Koehn, Gabriele ;
Weetman, Catherine .
ORGANOMETALLICS, 2011, 30 (21) :5556-5559
[3]   Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation [J].
Bart, SC ;
Lobkovsky, E ;
Chirik, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13794-13807
[4]   A tetrahedrally coordinated L3Fe-Nx platform that accommodates terminal nitride (FeIVN) and dinitrogen (FeI-N2-FeI) ligands [J].
Betley, TA ;
Peters, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6252-6254
[5]   Dinitrogen chemistry from trigonally coordinated iron and cobalt platforms [J].
Betley, TA ;
Peters, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10782-10783
[6]   Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].
Bull, James A. ;
Mousseau, James J. ;
Pelletier, Guillaume ;
Charette, Andre B. .
CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713
[7]   Abundant Metals Give Precious Hydrogenation Performance [J].
Bullock, R. Morris .
SCIENCE, 2013, 342 (6162) :1054-1055
[8]   Selective Hydrogenation of Nitriles to Secondary Imines Catalyzed by an Iron Pincer Complex [J].
Chakraborty, Subrata ;
Milstein, David .
ACS CATALYSIS, 2017, 7 (06) :3968-3972
[9]   Iron-Based Catalysts for the Hydrogenation of Esters to Alcohols [J].
Chakraborty, Sumit ;
Dai, Huiguang ;
Bhattacharya, Papri ;
Fairweather, Neil T. ;
Gibson, Michael S. ;
Krause, Jeanette A. ;
Guan, Hairong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) :7869-7872
[10]   A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles [J].
Chakraborty, Sumit ;
Brennessel, William W. ;
Jones, William D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8564-8567