Catalyst-Free α-Aminoxylation of 1,3-Dicarbonyl Compounds with TEMPO Using Selectfluor as an Oxidant

被引:6
作者
Tang, Lin [1 ]
Yang, Zhen [1 ]
Yang, Fang [1 ]
Huang, Yifan [1 ]
Chen, Hanfei [1 ]
Cheng, Hao [1 ]
Song, Weiyan [1 ]
Ren, Bo [1 ]
Zhou, Qiuju [1 ]
机构
[1] Xinyang Normal Univ, Coll Chem & Chem Engn, Xinyang 464000, Peoples R China
基金
中国国家自然科学基金;
关键词
catalyst-free; alpha-aminoxylation; 1; 3-dicarbonyl compounds; Selectfluor; C-O bond formation; C-H BOND; ELECTROPHILIC FLUORINATION; ENANTIOSELECTIVE SYNTHESIS; OXYAMINATION; ALDEHYDES; OXIDATION; CHEMISTRY; SOLVENT; WATER; KETONES;
D O I
10.1002/slct.201903856
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalyst-free and regioselective alpha-aminoxylation of 1,3-dicarbonyl compounds with TEMPO by use of Selectfluor as a mild oxidant has been demonstrated, yielding the corresponding alkoxyamines in good to excellent yields. The developed protocol features no employment of a catalyst, broad substrate scope and mild reaction conditions, which enables a convenient and efficient avenue for quaternary C-O bond formation.
引用
收藏
页码:12053 / 12056
页数:4
相关论文
共 68 条
[1]   anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense [J].
Abeykoon, Gayan A. ;
Chatterjee, Shreyosree ;
Chen, Jason S. .
ORGANIC LETTERS, 2014, 16 (12) :3248-3251
[2]   Peptide/Laccase Cocatalyzed Asymmetric α-Oxyamination of Aldehydes [J].
Akagawa, Kengo ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2011, 13 (13) :3498-3501
[3]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[4]   Catalyst-free and highly selective electrophilic mono-fluorination of acetoacetamides: facile and efficient preparation of 2-fluoroacetoacetamides in PEG-400 [J].
Bi, Jingjing ;
Zhang, Zhiguo ;
Liu, Qingfeng ;
Zhang, Guisheng .
GREEN CHEMISTRY, 2012, 14 (04) :1159-1162
[5]   Synthesis and evaluation of CC-1065 and duocarmycin analogues incorporating the iso-CI and iso-CBI alkylation subunits: Impact of relocation of the C-4 carbonyl [J].
Boger, DL ;
Garbaccio, RM ;
Jin, Q .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8875-8891
[6]   Organocatalyzed α-Oxyamination of Aldehydes Using Anodic Oxidation [J].
Bui, Nhat-Nguyen ;
Ho, Xuan-Huong ;
Mho, Sun-il ;
Jang, Hye-Young .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (31) :5309-5312
[7]   Translating solid state organic synthesis from a mixer mill to a continuous twin screw extruder [J].
Cao, Qun ;
Howard, Joseph L. ;
Crawford, Deborah E. ;
James, Stuart L. ;
Browne, Duncan L. .
GREEN CHEMISTRY, 2018, 20 (19) :4443-4447
[8]   General and Efficient a-Oxygenation of Carbonyl Compounds by TEMPO Induced by Single-Electron-Transfer Oxidation of Their Enolates [J].
Dinca, Emanuela ;
Hartmann, Philip ;
Smrcek, Jakub ;
Dix, Ina ;
Jones, Peter G. ;
Jahn, Ullrich .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) :4461-4482
[9]   Iron Chloride-Catalyzed Three-Component Domino Sequences: Syntheses of Functionalized α-Oxy-N-acylhemiaminals and α-Oxyimides [J].
Drouet, Fleur ;
Zhu, Jieping ;
Masson, Geraldine .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) :3563-3569
[10]   CAN-Catalyzed Rapid C-O Bond Formation towards α-Aminoxylation of Ketones [J].
Feng, Peng ;
Song, Song ;
Zhang, Li-He ;
Jiao, Ning .
SYNLETT, 2014, 25 (19) :2717-2720