Palladium-Catalyzed branch hydroaminocarbonylation of terminal alkynes with nitroarenes

被引：2

作者：

Yin, Zhiping ^{[1
]}

Yuan, Weiheng ^{[1
]}

Liu, Chenwei ^{[1
]}

Qin, Xiaowen ^{[1
]}

Xu, Tiefeng ^{[2
]}

Wu, Xiao-Feng ^{[3
]}

机构：

[1] Jiangsu Univ, Sch Pharm, Zhenjiang 212013, Peoples R China

[2] Zhejiang Sci Tech Univ, Natl Engn Lab Text Fiber Mat & Proc Technol Zhejia, Hangzhou 310018, Peoples R China

[3] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Liaoning, Peoples R China

来源：

JOURNAL OF CATALYSIS | 2024年 / 439卷

基金：

中国博士后科学基金;

关键词：

Hydroaminocarbonylation; Nitroarenes; Palladium catalysts; Terminal alkynes; (3-Unsaturated amides; ESCHERICHIA-COLI VITALITY; EXOGENOUS CARBON-MONOXIDE; ALPHA; BETA-UNSATURATED AMIDES; CARBONYLATIVE SYNTHESIS; NITROGEN LIGANDS; COMPLEXES; ALKENES; AMINOCARBONYLATION; NITROBENZENE; ACTIVATION;

D O I：

10.1016/j.jcat.2024.115781

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We report an innovative palladium-catalyzed hydroaminocarbonylation approach that efficiently converts nitroarenes and terminal alkynes into alpha,(3-unsaturated amides. This method, with broad substrate compatibility, delivers 32% to 87% yields with excellent regioselectivity. Central to the effectiveness of this reaction are the bipyridine ligand and salicylic acid, which play pivotal roles in optimizing both selectivity and product yield. Mechanistic experiments revealed that arylamine serves as a critical intermediate in the overall reaction, highlighting a unique pathway in the catalytic cycle. In contrast to conventional procedures, this protocol employs diverse nitroarenes and Mo(CO)6 as direct nitrogen and solid carbonyl sources, streamlining the process and enhancing safety by reducing the reliance on hazardous CO gas.

引用

页数：5

共 60 条

[1] Palladium-Catalyzed Denitrogenative Carbonylation of Benzotriazoles with Cr(CO)6 as the Carbonyl Source [J].

An, Tongshun ;

Liu, Chenwei ;

Yin, Yanzhao ;

Wu, Xiao-Feng ;

Yin, Zhiping .

ORGANOMETALLICS, 2022, 41 (13) :1731-1737

[2] Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

CHEMCATCHEM, 2009, 1 (01) :28-41

[3] Transition-metal-catalyzed transfer carbonylation with HCOOH or HCHO as non-gaseous C1 source [J].

Cao, Jian ;

Zheng, Zhan-Jiang ;

Xu, Zheng ;

Xu, Li-Wen .

COORDINATION CHEMISTRY REVIEWS, 2017, 336 :43-53

[4] Carbonylative synthesis of heterocycles involving diverse CO surrogates [J].

Chen, Zhengkai ;

Wang, Le-Cheng ;

Wu, Xiao-Feng .

CHEMICAL COMMUNICATIONS, 2020, 56 (45) :6016-6030

[5] Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes [J].

Cheung, Chi Wai ;

Ploeger, Marten Leendert ;

Hu, Xile .

CHEMICAL SCIENCE, 2018, 9 (03) :655-659

[6] HOMOGENEOUS CATALYSIS BY CATIONIC PALLADIUM COMPLEXES - PRECISION CATALYSIS IN THE CARBONYLATION OF ALKYNES [J].

DRENT, E ;

ARNOLDY, P ;

BUDZELAAR, PHM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) :57-63

[7] EFFICIENT PALLADIUM CATALYSTS FOR THE CARBONYLATION OF ALKYNES [J].

DRENT, E ;

ARNOLDY, P ;

BUDZELAAR, PHM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) :247-253

[8] A General and Selective Iron-Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl- and Cinnamides [J].

Driller, Katrin Marie ;

Prateeptongkum, Saisuree ;

Jackstell, Ralf ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :537-541

[9] Iron-Catalyzed Carbonylation: Selective and Efficient Synthesis of Succinimides [J].

Driller, Katrin Marie ;

Klein, Holger ;

Jackstell, Ralf ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6041-6044

[10] Selective Palladium-Catalyzed Aminocarbonylation of Olefins with Aromatic Amines and Nitroarenes [J].

Fang, Xianjie ;

Jackstell, Ralf ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14089-14093

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