Photochemical reductive deamination of alpha-amino aryl alkyl ketones

被引：3
作者：
Liang, Ji-Yuan [1 ,2 ,3 ]
Su, Yi-Wen [1 ,2 ,3 ]
Zou, You-Quan [1 ,2 ,3 ]
机构：
[1] Wuhan Univ, Zhongnan Hosp, Sch Pharmaceut Sci, Dept Otolaryngol, Wuhan 430071, Hubei, Peoples R China
[2] Wuhan Univ, Key Lab Combinatorial Biosynth & Drug Discovery, Minist Educ, Wuhan 430071, Hubei, Peoples R China
[3] Wuhan Univ, TaiKang Ctr Life & Med Sci, Wuhan 430071, Hubei, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 99期
关键词：
VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; FUNCTIONALIZATION; CLEAVAGE;
D O I：
10.1039/d3cc04837c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Photochemical reductive deamination of alpha-amino aryl alkyl ketones under photosensitizer-free conditions is presented. This protocol features high efficiency and selectivity. A plausible reaction pathway is proposed based on ultraviolet-visible absorption investigation, control experiments and deuterium-labelling studies. Mechanistic study reveals that the alpha-hydrogen atom of the ketone product originated from water. Photochemical reductive deamination of alpha-amino aryl alkyl ketones under photosensitizer-free conditions is presented, and this protocol features high efficiency and selectivity.
引用
收藏
页码：14685 / 14688
页数：4
相关论文
共 40 条
[1]   COOPERATIVE REACTIVITY IN PHOTOGENERATED RADICAL ION-PAIRS - PHOTOFRAGMENTATION OF AMINO KETONES [J].
BERGMARK, WR ;
WHITTEN, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4042-4043
[2]   UNUSUAL REDOX BEHAVIOR IN THE PHOTOINDUCED ELECTRON-TRANSFER REACTIONS OF AMINO KETONES [J].
BERGMARK, WR ;
DEWAN, C ;
WHITTEN, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8810-8812
[3]   Mechanistic Studies in Photocatalysis [J].
Buzzetti, Luca ;
Crisenza, Giacomo E. M. ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :3730-3747
[4]   Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings [J].
Chen, Bin ;
Wu, Li-Zhu ;
Tung, Chen-Ho .
ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (10) :2512-2523
[5]   Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1911-1923
[6]   Recent Developments on Understanding Charge Transfer in Molecular Electron Donor-Acceptor Systems [J].
Chen, Xi ;
Zhang, Xue ;
Xiao, Xiao ;
Wang, Zhijia ;
Zhao, Jianzhang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (16)
[7]   Recent advances in transition metal-free annulation toward heterocycle diversity based on the C-N bond cleavage of enaminone platform [J].
Chen, Xiao Yun ;
Zhang, Xiaotong ;
Wan, Jie-Ping .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (12) :2356-2369
[8]   Visible-light induced dearomatization reactions [J].
Cheng, Yuan-Zheng ;
Feng, Zuolijun ;
Zhang, Xiao ;
You, Shu-Li .
CHEMICAL SOCIETY REVIEWS, 2022, 51 (06) :2145-2170
[9]   Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes [J].
Crisenza, Giacomo E. M. ;
Mazzarella, Daniele ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5461-5476
[10]   3d Transition Metals for C-H Activation [J].
Gandeepan, Parthasarathy ;
Mueller, Thomas ;
Zell, Daniel ;
Cera, Gianpiero ;
Warratz, Svenja ;
Ackermann, Lutz .
CHEMICAL REVIEWS, 2019, 119 (04) :2192-2452
1234