Organocatalyzed Aerobic Oxidation of Aldehydes to Acids

被引：57

作者：

Dai, Peng-Fei ^{[1
]}

Qu, Jian-Ping ^{[2
]}

Kang, Yan-Biao ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

基金：

中国国家自然科学基金;

关键词：

TERT-BUTYL NITRITE; CARBOXYLIC-ACIDS; MOLECULAR-OXYGEN; PRIMARY ALCOHOLS; METAL-FREE; CLEAVAGE;

D O I：

10.1021/acs.orglett.9b00101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example organocatalyzed aerobic oxidation of aldehydes to carboxylic acids in both organic solvent and water under mild conditions is developed. As low as 5 mol % N-hydroxyphthalimide was used as the organocatalyst, and molecular O-2 was used as the sole oxidant. No transition metals or hazardous oxidants or cocatalysts were involved. A wide range of carboxylic acids bearing diverse functional groups were obtained from aldehydes, even from alcohols, in high yields.

引用

页码：1393 / 1396

页数：4

共 31 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
BAL, BS
CHILDERS, WE
PINNICK, HW
[J]. TETRAHEDRON, 1981, 37 (11) : 2091 - 2096
[2] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS
BOWDEN, K
HEILBRON, IM
JONES, ERH
WEEDON, BCL
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN): : 39 - 45
[3] DESIGNING LIGANDS FOR OXIDIZING COMPLEXES
COLLINS, TJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (09) : 279 - 285
[4] Fehling H., 1849, ANN CHEM PHARM, V72, P106, DOI DOI 10.1002/JLAC.18490720112
[5] Selective Aerobic Oxidation of Alcohols to Aldehydes, Carboxylic Acids, and Imines Catalyzed by a Ag-NHC Complex
Han, Lei
Xing, Ping
Jiang, Biao
[J]. ORGANIC LETTERS, 2014, 16 (13) : 3428 - 3431
[6] HEYNS K, 1947, LIEBIGS ANN CHEM, V558, P177
[7] A new route to lactam precursors from cycloalkanes:: Direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide
Hirabayashi, T
Sakaguchi, S
Ishii, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1120 - 1123
[8] Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate catalyzed oxidation
Hunsen, M
[J]. SYNTHESIS-STUTTGART, 2005, (15): : 2487 - 2490
[9] Selective aerobic oxidation of activated alcohols into acids or aldehydes in ionic liquids
Jiang, Nan
Ragauskas, Arthur J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) : 7030 - 7033
[10] Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids
Jiang, Xingguo
Zhang, Jiasheng
Ma, Shengming
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8344 - 8347

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