Electro-oxidative Intermolecular Allylic C(sp3)-H Aminations

被引:22
作者
Wang, Yulei [1 ,2 ]
Lin, Zhipeng [1 ,2 ]
Oliveira, Joao C. A. [1 ,2 ]
Ackermann, Lutz [1 ,2 ]
机构
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Georg August Univ Gottingen, Wohler Res Inst Sustainable Chem WISCh, D-37077 Gottingen, Germany
关键词
C-H FUNCTIONALIZATION; ALCOHOLS; ELECTROCHEMISTRY; ELECTROSYNTHESIS; STRATEGIES; AMINES; BONDS; HYDROXYPHTHALIMIDE; ALLYLATION; ANILINES;
D O I
10.1021/acs.joc.1c00682
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative intermolecular nitrogenation of C(sp(3))-H bonds represents one of the most straightforward strategies to construct nitrogen-containing molecules. However, a sacrificial chemical oxidant is generally required. Herein, we describe electrochemical oxidative intermolecular allylic C(sp(3))-H aminations in an undivided cell by electric current. The cross-dehydrogenative amination proceeded efficiently with ample scope under metal-and chemical oxidant-free reaction conditions, giving molecular H-2 as the only byproduct.
引用
收藏
页码:15935 / 15945
页数:11
相关论文
共 66 条
[1]   Metalla-electrocatalyzed C-H Activation by Earth-Abundant 3d Metals and Beyond [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (01) :84-104
[2]   Electrochemically Oxidative C-C Bond Cleavage of Alkylarenes for Anilines Synthesis [J].
Adeli, Yeerlan ;
Huang, Kaimeng ;
Liang, Yujie ;
Jiang, Yangye ;
Liu, Jianzhong ;
Song, Song ;
Zeng, Cheng-Chu ;
Jiao, Ning .
ACS CATALYSIS, 2019, 9 (03) :2063-2067
[3]  
AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737
[4]  
[Anonymous], 2020, EUR J ORG CHEM
[5]   Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates [J].
Burman, Jacob S. ;
Blakey, Simon B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) :13666-13669
[6]   Implanting Nitrogen into Hydrocarbon Molecules through C-H and C-C Bond Cleavages: A Direct Approach to Tetrazoles [J].
Chen, Feng ;
Qin, Chong ;
Cui, Yuxin ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) :11487-11491
[7]   Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines [J].
Cheng, Qiang ;
Chen, Junting ;
Lin, Songyun ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (41) :17287-17293
[8]   Discovery of the Dual Orexin Receptor Antagonist [(7R)-4-(5-Chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the Treatment of Insomnia [J].
Cox, Christopher D. ;
Breslin, Michael J. ;
Whitman, David B. ;
Schreier, John D. ;
McGaughey, Georgia B. ;
Bogusky, Michael J. ;
Roecker, Anthony J. ;
Mercer, Swati P. ;
Bednar, Rodney A. ;
Lemaire, Wei ;
Bruno, Joseph G. ;
Reiss, Duane R. ;
Harrell, C. Meacham ;
Murphy, Kathy L. ;
Garson, Susan L. ;
Doran, Scott M. ;
Prueksaritanont, Thomayant ;
Anderson, Wayne B. ;
Tang, Cuyue ;
Roller, Shane ;
Cabalu, Tamara D. ;
Cui, Donahui ;
Hartman, George D. ;
Young, Steven D. ;
Koblan, Ken S. ;
Winrow, Christopher J. ;
Renger, John J. ;
Coleman, Paul J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (14) :5320-5332
[9]   Anodic Cyclization Reactions and the Mechanistic Strategies That Enable Optimization [J].
Feng, Ruozhu ;
Smith, Jake A. ;
Moeller, Kevin D. .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) :2346-2352
[10]   Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].
Francke, Robert ;
Little, R. Daniel .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521