Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes

被引：28

作者：

Budweg, Svenja ^{[1
]}

Junge, Kathrin ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Leibniz Inst Katalyse eV, Univ Rostock, Albert Einstein Str 29a, D-18059 Rostock, Germany

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 94期

关键词：

OPPENAUER-TYPE OXIDATION; HYDROGENATION; (DE)HYDROGENATION; RUTHENIUM; LIGANDS; IRON;

D O I：

10.1039/c9cc07337j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.

引用

页码：14143 / 14146

页数：4

共 43 条

[1] First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands [J].

Alig, Lukas ;

Fritz, Maximilian ;

Schneider, Sven .

CHEMICAL REVIEWS, 2019, 119 (04) :2681-2751

[2] Ruthenium(II)-catalyzed Oppenauer-type oxidation of secondary alcohols [J].

Almeida, MLS ;

Beller, M ;

Wang, GZ ;

Backvall, JE .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1533-1536

[3]

Backvall J.-E., 2010, MODERN OXIDATION MET, V2nd, P147, DOI DOI 10.1002/9783527632039.CH5

[4] RUTHENIUM-CATALYZED AEROBIC OXIDATION OF ALCOHOLS VIA MULTISTEP ELECTRON-TRANSFER [J].

BACKVALL, JE ;

CHOWDHURY, RL ;

KARLSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) :473-475

[5] Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst [J].

Bruneau-Voisine, Antoine ;

Wang, Ding ;

Dorcet, Vincent ;

Roisnel, Thierry ;

Darcel, Christophe ;

Sortais, Jean-Baptiste .

ORGANIC LETTERS, 2017, 19 (13) :3656-3659

[6] Iron-PNP-Pincer-Catalyzed Transfer Dehydrogenation of Secondary Alcohols [J].

Budweg, Svenja ;

Wei, Zhihong ;

Jiao, Haijun ;

Junge, Kathrin ;

Beller, Matthias .

CHEMSUSCHEM, 2019, 12 (13) :2988-2993

[7] Iron-Catalyzed Oppenauer-Type Oxidation of Alcohols [J].

Coleman, Michael G. ;

Brown, Alec N. ;

Bolton, Brett A. ;

Guan, Hairong .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :967-970

[8] Homogeneous Transition Metal Catalysis of Acceptorless Dehydrogenative Alcohol Oxidation: Applications in Hydrogen Storage and to Heterocycle Synthesis [J].

Crabtree, Robert H. .

CHEMICAL REVIEWS, 2017, 117 (13) :9228-9246

[9] Manganese-Catalyzed Multicomponent Synthesis of Pyrimidines from Alcohols and Amidines [J].

Deibl, Nicklas ;

Kempe, Rhett .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (06) :1663-1666

[10] C-Alkylation of Secondary Alcohols by Primary Alcohols through Manganese-Catalyzed Double Hydrogen Autotransfer [J].

El-Sepelgy, Osama ;

Matador, Esteban ;

Brzozowska, Aleksandra ;

Rueping, Magnus .

CHEMSUSCHEM, 2019, 12 (13) :3099-3102

← 1 2 3 4 5 →