Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature

被引：16

作者：

Fang, Zheng ^{[1
]}

Hu, Wen-Li ^{[1
]}

Liu, De-Yong ^{[1
]}

Yu, Chu-Yi ^{[1
,2
]}

Hu, Xiang-Guo ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

[2] Chinese Acad Sci, BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

来源：

GREEN CHEMISTRY | 2017年 / 19卷 / 05期

关键词：

CHEMISTRY; 1,2,4,5-TETRAZINES; MONOFLUOROALKENES; CYCLOADDITIONS; FLUORINATION; LIGATION; REAGENTS; FLUORIDE; ACCESS; BOND;

D O I：

10.1039/c6gc03494b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and green procedure for the synthesis of tetrazines has been developed based on an old chemistry reported by Carboni in 1958. Both symmetric and asymmetric 3,6-disubstituted 1,2,4,5-tetrazines can be obtained in moderate to high yields from the corresponding gem-difluoroalkenes under aerobic conditions at room temperature. This work represents a rare example that ambient air is utilized as an oxidant for the synthesis of tetrazines.

引用

页码：1299 / 1302

页数：4

共 50 条

[41] Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water
Hu, Jiefeng
Han, Xiaowei
Yuan, Yu
Shi, Zhuangzhi
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13342 - 13346
[42] Synthesis of gem-Difluoroalkenes via a Sequence of Hydroboration and 1,2-Elimination of α,β-Unsaturated Carbonyls
An, Shiyun
Zhang, Jinlong
Jiang, Gaoxi
[J]. SYNLETT, 2021, 32 (01) : 91 - 94
[43] Electroreductive Cross-Coupling of Trifluoromethyl Alkenes and Redox Active Esters for the Synthesis of Gem-Difluoroalkenes
Claraz, Aurelie
Allain, Clemence
Masson, Geraldine
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (02)
[44] Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process
Zhang, Haoxiang
Liang, Mengze
Zhang, Xiao
He, Meng-Ke
Yang, Chao
Guo, Lin
Xia, Wujiong
[J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 9 (01) : 95 - 101
[45] Synthesis of difluoromethylated benzylborons via rhodium(Ⅰ)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes
Yuanhong Cai
Donghang Tan
Qiqi Zhang
Wenxin Lv
Qingjiang Li
Honggen Wang
[J]. Chinese Chemical Letters, 2021, 32 (01) : 417 - 420
[46] Synthesis of fluorovinyl pyrazolyl (thio)ethers by the reaction of gem-difluoroalkenes with pyrazolin-5-ones (thiones)
Huang, Tao
Zhao, Xianghu
Ji, Xinfei
Wu, Wei
Cao, Song
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2016, 182 : 61 - 68
[47] Synthesis of N,N-disubstituted 2-aminothiophenes by the cyclization of gem-difluoroalkenes with β-keto thioamides
Zhang, Xuxue
Wu, Mingsheng
Zhang, Juan
Cao, Song
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (11) : 2436 - 2442
[48] A CONCISE SYNTHESIS OF FUNCTIONALIZED GEM-DIFLUOROALKENES VIA THE ADDITION OF ORGANOLITHIUM REAGENTS TO ALPHA-TRIFLUOROMETHYLSTYRENE
BEGUE, JP
BONNETDELPON, D
ROCK, MH
[J]. TETRAHEDRON LETTERS, 1995, 36 (28) : 5003 - 5006
[49] Synthesis of Monofluorocyclohexene via Photocatalytic Defluorinative [4+2] Annulation of gem-Difluoroalkenes with Unactivated Alkenes
Zhang, Guang-Xu
Li, Dong-Sheng
Xue, Fei
Chen, An-Feng
Deng, Hong-Ping
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4603 - 4608
[50] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling
Lan, Yun
Yang, Feiyan
Wang, Chuan
[J]. ACS CATALYSIS, 2018, 8 (10): : 9245 - 9251

← 1 2 3 4 5 →