Transition-Metal-Catalyzed Hydroaminocarbonylations of Alkenes and Alkynes

被引:64
作者
Cai, Shoule [1 ,2 ]
Zhang, Haocheng [1 ,2 ]
Huang, Hanmin [1 ,2 ,3 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Peoples R China
来源
TRENDS IN CHEMISTRY | 2021年 / 3卷 / 03期
基金
中国国家自然科学基金;
关键词
REGIOSELECTIVE SYNTHESIS; AMINOCARBONYLATION; OLEFINS; CYCLOCARBONYLATION; CARBONYLATION; AMINES; BONDS; AMIDE; HYDROAMIDOCARBONYLATION; PALLADIUM(II);
D O I
10.1016/j.trechm.2020.11.006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
While the amide bond is one of the most widespread backbones in natural peptides, pharmaceuticals, and agrochemicals, the atom-economic synthesis of amides remains a major challenge in organic chemistry. In this context, transition-metal-catalyzed hydroaminocarbonylation of cost-effective alkenes and alkynes has emerged as an ideal approach to access amides. However, it is only in recent times that more chemo- and regioselective hydroaminocarbonylation transformations, covering large substrate scope and under milder conditions, have been reported. In this review, we highlight some recent contributions to this field and elucidate the impact of ligands on regioselectivity, as well as discuss the potential applications of abundantly available nitrogen sources for hydroaminocarbonylation.
引用
收藏
页码:218 / 230
页数:13
相关论文
共 47 条
[1]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[2]   Some aspects of the properties and degradation of polyacrylamides [J].
Caulfield, MJ ;
Qiao, GG ;
Solomon, DH .
CHEMICAL REVIEWS, 2002, 102 (09) :3067-3083
[3]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[4]   Nonclassical Routes for Amide Bond Formation [J].
de Figueiredo, Renata Marcia ;
Suppo, Jean-Simon ;
Campagne, Jean-Marc .
CHEMICAL REVIEWS, 2016, 116 (19) :12029-12122
[5]   Enantioselective cyclocarbonylation of 2-vinylanilines to six-membered ring lactams [J].
Dong, C ;
Alper, H .
TETRAHEDRON-ASYMMETRY, 2004, 15 (01) :35-40
[6]   Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N-H Bonds in Aliphatic Amines [J].
Dong, Kaiwu ;
Fang, Xianjie ;
Jackstell, Ralf ;
Laurenczy, Gabor ;
Li, Yuehui ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) :6053-6058
[7]   Catallytic and regioselective synthesis of gem- or trans-α,β-unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine [J].
El Ali, B ;
Tijani, J .
APPLIED ORGANOMETALLIC CHEMISTRY, 2003, 17 (12) :921-931
[8]   Total regioselective control of the carbonylative coupling of 1-heptyne with aniline and N-methyl aniline catalyzed by palladium(II) and phosphine ligand [J].
El Ali, B ;
Tijani, J ;
El-Ghanam, AM .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 187 (01) :17-33
[9]   Regioselective palladium(II)-catalyzed synthesis of five- or seven-membered ring lactones and five-, six- or seven-membered ring lactams by cyclocarbonylation methodology [J].
ElAli, B ;
Okuro, K ;
Vasapollo, G ;
Alper, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4264-4270
[10]   Selective Palladium-Catalyzed Aminocarbonylation of 1,3-Dienes: Atom-Efficient Synthesis of β,γ-Unsaturated Amides [J].
Fang, Xianjie ;
Li, Haoquan ;
Jackstell, Ralf ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :16039-16043