Palladium-Catalyzed Aerobicα,β-Dehydrogenation of Aliphatic Amides

被引：6

作者：

Keerthana, Meledath Sudhakaran ^{[1
]}

Jeganmohan, Masilamani ^{[1
]}

机构：

[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 07期

关键词：

C-H ACTIVATION; AEROBIC DEHYDROGENATION; ALKANE DEHYDROGENATION; ALPHA; BETA-UNSATURATED KETONES; CARBOXYLIC-ACIDS; EFFICIENT ACCESS; BOND ACTIVATION; DIRECTING GROUP; LIGHT ALKANES; ALDEHYDES;

D O I：

10.1021/acs.joc.2c00226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)-catalyzed alpha,beta-dehydrogenation of sub-stituted aliphatic amides assisted by a reusable bis-chelating 8-aminoquinoline ligand is demonstrated. Broad spectra of beta-substituted including olefin-substituted aliphatic amides are welltolerated. The present protocol efficiently dehydrogenates the lessacidic aliphatic amidesviathe chelation-assisted beta-C-H bondactivation and replaces the traditional enolate-based strategy.

引用

页码：4873 / 4882

页数：10

共 61 条

[1] Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ORGANIC LETTERS, 2011, 13 (12) :3278-3281

[2] Regeneration of an Iridium(III) Complex Active for Alkane Dehydrogenation Using Molecular Oxygen [J].

Allen, Kate E. ;

Heinekey, D. Michael ;

Goldman, Alan S. ;

Goldberg, Karen I. .

ORGANOMETALLICS, 2014, 33 (06) :1337-1340

[3] Selenium dioxide, a new oxidising agent Part III Its reaction with some alcohols and esters [J].

Astin, S ;

Newman, ACC ;

Riley, HL .

JOURNAL OF THE CHEMICAL SOCIETY, 1933, :391-394

[4] Cobalt catalyzed carbonylation of unactivated C(sp3)-H bonds [J].

Barsu, Nagaraju ;

Bolli, Shyam Kumar ;

Sundararaju, Basker .

CHEMICAL SCIENCE, 2017, 8 (03) :2431-2435

[5] Branching Regulation in Olefin Polymerization via Lewis Acid Triggered Isomerization of Monomers [J].

Basbug Alhan, Hatice E. ;

Jones, Glen R. ;

Harth, Eva .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (12) :4743-4749

[6]

BerteinaRaboin S., 2022, CATALYSTS, V12, P86

[7] Terminal Olefins to Linear α,β-Unsaturated Ketones: Pd(II)/Hypervalent Iodine Co-catalyzed Wacker Oxidation-Dehydrogenation [J].

Bigi, Marinus A. ;

White, M. Christina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) :7831-7834

[8] Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization [J].

Chen, Yifeng ;

Huang, David ;

Zhao, Yizhou ;

Newhouse, Timothy R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (28) :8258-8262

[9] 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

[10] 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

← 1 2 3 4 5 6 7 →