Photoredox-Enabled Synthesis of α-Alkylated Alkenylammonium Salts

被引：0

作者：

Tonedachi, Rina ^{[1
]}

Yoshita, Aoi ^{[1
]}

Sakakibara, Yota ^{[1
]}

Murakami, Kei ^{[1
,2
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Gakuen Uegahara 1, Sanda, Hyogo 6691330, Japan

[2] JST PRESTO, 7 Gobancho,Chiyoda, Tokyo 1020076, Japan

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 21期

基金：

日本科学技术振兴机构;

关键词：

alkenylammonium salts; photoredox catalyst; alkylation; halogen-atom transfer; quaternary ammonium salts; ATOM TRANSFER; RADICALS; GENERATION;

D O I：

10.1055/a-2302-5887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of novel synthetic methods for quaternary ammonium salts is highly demanded since the current synthesis heavily relies on the conventional Menshutkin reaction. Herein, we report photoredox-catalyzed alkylation of alpha-brominated alkenylammonium salts. Mechanistically, the generation of a highly reactive alpha-ammoniovinyl radical is the key to our method. This reaction enables thesynthesis of various unprecedented alpha-alkylated alkenylammonium salts.

引用

页码：3341 / 3347

页数：7

共 50 条

[31] Regiospecific Synthesis of 1-Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion
Cheng, Yuanzheng
Yuan, Xiangai
Jiang, Heng
Wang, Ruzhi
Ma, Jing
Zhang, Yan
Yu, Shouyun
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2859 - 2866
[32] Photoredox-catalysed regioselective synthesis of C-4-alkylated pyridines with N-(acyloxy)phthalimides
Zhang, Zhucheng
He, Qian
Zhang, Xiaofei
Yang, Chunhao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (09) : 1969 - 1973
[33] Photoredox/NHC Dual Catalysis Enabled de Novo Synthesis of α-Amino Acids Derivatives
Ji, Dong-Sheng
Zhou, Chenxing
Zhang, Xin
Ye, Youwan
Bao, Xiazhen
Yuan, Yong
Huo, Congde
ORGANIC LETTERS, 2024, 26 (39) : 8435 - 8440
[34] Distal Amidoketone Synthesis Enabled by Dimethyl Benziodoxoles via Dual Copper/Photoredox Catalysis
Ge, Yuanyuan
Shao, Yingbo
Wu, Shuang
Liu, Pan
Li, Junzhao
Qin, Hanzhang
Zhang, Yanxia
Xue, Xiao-song
Chen, Yiyun
ACS CATALYSIS, 2023, 13 (06) : 3749 - 3756
[35] One-Pot Synthesis of C3-Alkylated Imidazopyridines from α-Bromocarbonyls under Photoredox Conditions
Tong, Jinwen
Zhan, Yanling
Li, Jingyu
Liu, Ping
Sun, Peipei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (32) : 4541 - 4545
[36] Deaminative defluoroalkylation of α-trifluoromethylalkenes enabled by photoredox catalysis
Zhang, Guodong
Wang, Lei
Cui, Liping
Gao, Pan
Chen, Feng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (02) : 294 - 299
[37] Expedient Trifluoromethylacylation of Styrenes Enabled by Photoredox Catalysis
Wang, Lu
Zhang, Heng
Zhu, Chuan
Feng, Chao
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (01): : 59 - 64
[38] Acyldifluoromethylation Enabled by NHC-Photoredox Cocatalysis
Zhang, Bei
Wang, Jian
ORGANIC LETTERS, 2022, 24 (20) : 3721 - 3725
[39] Dual Photoredox and Cobalt Catalysis Enabled Transformations
Bajya, Kalu Ram
Selvakumar, Sermadurai
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (20)
[40] ALKENYLAMMONIUM SALTS AS DIENOPHILES IN DIELS-ALDER REACTIONS - FURTHER INVESTIGATIONS ON THE STEREOCHEMICAL COURSE OF THE REACTION
JUNG, ME
BUSZEK, KR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 40 - ORGN

← 1 2 3 4 5 →