Electron Donor-Acceptor Complex-Initiated Photochemical Cyanation for the Preparation of α-Amino Nitriles

被引：33

作者：

Xia, Qing ^{[1
]}

Li, Yufei ^{[1
]}

Cheng, Lan ^{[1
]}

Liang, Xin ^{[1
]}

Cao, Chenlin ^{[1
]}

Dai, Peng ^{[1
]}

Deng, Hongping ^{[1
]}

Zhang, Weihua ^{[1
]}

Wang, Qingmin ^{[2
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Peoples R China

[2] Nankai Univ, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, State Key Lab Elementoorgan Chem,Res Inst Element, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 24期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

C-H BOND; STRECKER REACTION; TERTIARY-AMINES; C(SP(3))-H BONDS; LIGHT; ALKYLATION; CYANIDE; FUNCTIONALIZATION; ALDEHYDES; KETONES;

D O I：

10.1021/acs.orglett.0c03703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An electron donor-acceptor complex-initiated alpha-cyanation of tertiary amines has been described. The reaction protocol provides a novel method to synthesize various alpha-amino nitriles under mild conditions. The reaction can proceed smoothly without the presence of photocatalysts and transition metal catalysts, and either oxidants are unnecessary or O-2 is the only oxidant. The practicality of this method is showcased not only by the late-stage functionalization of natural alkaloid derivatives and pharmaceutical intermediate, but also by the applicability of a stop-flow microtubing reactor.

引用

页码：9638 / 9643

页数：6

共 50 条

[1] An electron donor-acceptor complex-initiated C-H trifluoromethylation and perfluoroalkylation of enamides and quinoxalinones
Song, Yaqi
Sun, Tian-Yu
Xia, Xiao-Feng
Wang, Dawei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (41) : 8317 - 8322
[2] Radical Alkynyltrifluoromethylation of Alkenes Initiated by an Electron Donor-Acceptor Complex
Jiang, Heng
He, Yanyan
Cheng, Yuanzheng
Yu, Shouyun
ORGANIC LETTERS, 2017, 19 (05) : 1240 - 1243
[3] Electron Donor-Acceptor Complex Initiated Photochemical Phosphorus Arylation with Diaryliodonium Salts toward the Synthesis of Phosphine Oxides
Bugaenko, Dmitry I.
Karchava, Alexander V.
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (11) : 1893 - 1900
[4] Decarboxylative cyanation and thiocyanation via catalytic electron donor-acceptor complex with copper catalysis
Zhao, Hongping
Xi, Xiaoxiang
Wu, Tianbao
Chen, Zimin
Wang, Minyan
Yuan, Weiming
SCIENCE CHINA-CHEMISTRY, 2024, 67 (09) : 3019 - 3028
[5] Decarboxylative cyanation and thiocyanation via catalytic electron donor-acceptor complex with copper catalysis
Hongping Zhao
Xiaoxiang Xi
Tianbao Wu
Zimin Chen
Minyan Wang
Weiming Yuan
Science China(Chemistry), 2024, 67 (09) : 3019 - 3028
[6] Visible-light-induced electron donor-acceptor (EDA) complex-initiated synthesis of non-anomeric S-aryl glycosides
Hou, Jin-Yu
Zhang, Le
He, Shi-Yun
Ye, Mei-Ling
Chen, Jian
Huang, Tian-Le
Lv, Guang-Hui
Hai, Li
Yang, Zhong-Zhen
Wu, Yong
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (24) : 6200 - 6204
[7] POLYMERIZATION INITIATED BY AN ELECTRON DONOR-ACCEPTOR COMPLEX .3. POLYMERIZATION OF METHYL METHACRYLATE INITIATED IN SYSTEMS CONTAINING POLYMER ELECTRON DONOR, ACCEPTOR, AND CARBON TETRACHLORIDE
MATSUDA, M
ISHIOROS.Y
MAKROMOLEKULARE CHEMIE, 1969, 126 (JUL): : 16 - &
[8] Cycloadditions of Donor-Acceptor Cyclopropanes and Nitriles
Pagenkopf, Brian L.
Vemula, Naresh
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2561 - 2567
[9] Enhanced basicity of an electron donor-acceptor complex
Stevenson, Bernard G. G.
Prascsak, Amanada V. V.
Lee, Annemarie A. A.
Talbott, Eric D. D.
Fredin, Lisa A. A.
Swierk, John R. R.
CHEMICAL COMMUNICATIONS, 2023, 59 (20) : 2943 - 2945
[10] An in situ generated proton initiated aromatic fluoroalkylation via electron donor-acceptor complex photoactivation
Huang, Panyi
Lv, Chun
Song, Haijing
Wang, Chenjing
Du, Junze
Li, Jianjun
Sun, Bin
Jin, Can
GREEN CHEMISTRY, 2024, 26 (12) : 7198 - 7205

← 1 2 3 4 5 →