Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines

被引:141
作者
Zhou, Nengneng [1 ]
Yuan, Xiang-Ai [2 ]
Zhao, Yue [1 ]
Xie, Jin [1 ]
Zhu, Chengjian [1 ,3 ]
机构
[1] Nanjing Univ, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat, Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China
[2] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Peoples R China
[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
C-B coupling; hydroboration; imines; photochemistry; radicals; HETEROCYCLIC CARBENE-BORANES; C-H BONDS; AMINO BORONATE ESTERS; VISIBLE-LIGHT; RADICAL REACTIONS; BORYL RADICALS; PINACOLBORYL ADDITION; CARBONYL DERIVATIVES; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS;
D O I
10.1002/anie.201800421
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic inverse hydroboration of imines with N-heterocyclic carbene (NHC) boranes has been realized by means of cooperative organocatalysis and photocatalysis. This catalytic combination provides a promising platform for promoting NHC-boryl radical chemistry under sustainable and radical-initiator-free conditions. The highly important functional-group compatibility and possible application in late-stage hydroborations represent an important step forward to an enhanced alpha-amino organoboron library.
引用
收藏
页码:3990 / 3994
页数:5
相关论文
共 68 条
[1]   Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes [J].
Adams, Matt R. ;
Tien, Chieh-Hung ;
McDonald, Robert ;
Speed, Alexander W. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (52) :16660-16663
[2]   Diazaphospholene Precatalysts for Imine and Conjugate Reductions [J].
Adams, Matt R. ;
Tien, Chieh-Hung ;
Huchenski, Blake S. N. ;
Ferguson, Michael J. ;
Speed, Alexander W. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6268-6271
[3]   Synthesis of α-aminoboronic acids [J].
Andres, Patricia ;
Ballano, Gema ;
Calaza, M. Isabel ;
Cativiela, Carlos .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2291-2307
[4]   COINAGE METAL-CATALYZED HYDROBORATION OF IMINES [J].
BAKER, RT ;
CALABRESE, JC ;
WESTCOTT, SA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 498 (02) :109-117
[5]   Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines [J].
Beenen, Melissa A. ;
An, Chihui ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6910-+
[6]   A NEW TECHNIQUE FOR THE CONVERSION OF OLEFINS INTO ORGANOBORANES AND RELATED ALCOHOLS [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (21) :5694-5695
[7]   Metal-free catalytic hydrogenation [J].
Chase, Preston A. ;
Welch, Gregory C. ;
Jurca, Titel ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053
[8]   Catalytic Hydroboration of Carbonyl Derivatives, Imines, and Carbon Dioxide [J].
Chong, Che Chang ;
Kinjo, Rei .
ACS CATALYSIS, 2015, 5 (06) :3238-3259
[9]   Synthesis and Reactions of N-Heterocyclic Carbene Boranes [J].
Curran, Dennis P. ;
Solovyev, Andrey ;
Brahmi, Malika Makhlouf ;
Fensterbank, Louis ;
Malacria, Max ;
Lacote, Emmanuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) :10294-10317
[10]   Boron chemistry in a new light [J].
Duret, Guillaume ;
Quinlan, Robert ;
Bisseret, Philippe ;
Blanchard, Nicolas .
CHEMICAL SCIENCE, 2015, 6 (10) :5366-5382