Iron-Catalyzed α,β-Dehydrogenation of Carbonyl Compounds

被引：41

作者：

Zhang, Xiao-Wei ^{[1
,2
]}

Jiang, Guo-Qing ^{[1
]}

Lei, Shu-Hui ^{[1
]}

Shan, Xiang-Huan ^{[2
]}

Qu, Jian-Ping ^{[1
]}

Kang, Yan-Biao ^{[2
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Peoples R China

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

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 05期

基金：

中国国家自然科学基金;

关键词：

AEROBIC DEHYDROGENATION; ALPHA; BETA-UNSATURATED ALDEHYDES; OXIDATION; ALCOHOLS; NITRATE/TEMPO; KETONES; ENONES; TEMPO;

D O I：

10.1021/acs.orglett.1c00043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron-catalyzed alpha,beta-dehydrogenation of carbonyl com-pounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their alpha,beta-unsaturated counterparts in a simple one-step reaction with high yields.

引用

页码：1611 / 1615

页数：5

共 29 条

[1] Iron-catalyzed dehydrogenation reactions and their applications in sustainable energy and catalysis [J].

Balaraman, Ekambaram ;

Nandakumar, Avanashiappan ;

Jaiswal, Garima ;

Sahoo, Manoj K. .

CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (15) :3177-3195

[2] Iron Catalysis in Organic Synthesis [J].

Bauer, Ingmar ;

Knoelker, Hans-Joachim .

CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387

[3] SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS [J].

BHATTACHARYA, A ;

DIMICHELE, LM ;

DOLLING, UH ;

DOUGLAS, AW ;

GRABOWSKI, EJJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3318-3319

[4] Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions [J].

Chen, Ming ;

Dong, Guangbin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (37) :14889-14897

[5] Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones [J].

Chen, Ming ;

Rago, Alexander J. ;

Dong, Guangbin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (49) :16205-16209

[6] Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide [J].

Chen, Yifeng ;

Turlik, Aneta ;

Newhouse, Timothy R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (04) :1166-1169

[7] Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles [J].

Chen, Yifeng ;

Romaire, Justin P. ;

Newhouse, Timothy R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) :5875-5878

[8] Aerobic Dehydrogenation of Cyclohexanone to Cyclohexenone Catalyzed by Pd(DMSO)2(TFA)2: Evidence for Ligand-Controlled Chemoselectivity [J].

Diao, Tianning ;

Pun, Doris ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (22) :8205-8212

[9] Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd (TFA)2/4,5-diazafluorenone catalyst [J].

Diao, Tianning ;

Wadzinski, Tyler J. ;

Stahl, Shannon S. .

CHEMICAL SCIENCE, 2012, 3 (03) :887-891

[10] Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones [J].

Diao, Tianning ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14566-14569

← 1 2 3 →