Synthetic Access to Secondary Propargylamines via a Copper-Catalyzed Oxidative Deamination/Alkynylation Cascade

被引：20

作者：

Li, Huiqiong ^{[1
]}

Feng, Huangdi ^{[1
]}

Zhang, Jingxian ^{[1
]}

Van Der Eycken, Erik V. ^{[2
,3
]}

Huang, Liliang ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, 333 Longteng Rd, Shanghai 201620, Peoples R China

[2] Katholieke Univ Leuven, Lab Organ & Microwave Assisted Chem, Dept Chem, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[3] Peoples Friendship Univ Russia, RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 16期

关键词：

ALDEHYDE-ALKYNE-AMINE; AEROBIC OXIDATION; TERTIARY-AMINES; TERMINAL ALKYNES; EFFICIENT; IMINES; METAL; HYDROAMINATION; ACTIVATION; HETEROCYCLES;

D O I：

10.1021/acs.joc.9b01431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and selective cascade reaction of primary amines and alkynes for the synthesis of the corresponding secondary propargylamines is described. This protocol proceeds with a CuBr2/TBHP system through a process of oxidative deamination of primary amines to imine and alkynylation, featuring a wide scope of substrates with good functional-group tolerance and operational simplicity. Additionally, the use of two different primary amines could also work smoothly using this protocol.

引用

页码：10501 / 10508

页数：8

共 52 条

[1] Reaction pathways over copper and cerium oxide catalysts for direct synthesis of imines from amines under aerobic conditions [J].

Al-Hmoud, Linda ;

Jones, Christopher W. .

JOURNAL OF CATALYSIS, 2013, 301 :116-124

[2] Cross-Dehydrogenative Coupling of Tertiary Amines and Terminal Alkynes Catalyzed by Copper Nanoparticles on Zeolite [J].

Alonso, Francisco ;

Arroyo, Adrian ;

Martin-Garcia, Iris ;

Moglie, Yanina .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) :3549-3561

[3] Chemical fixation of CO2 to N-propargylamines: A straightforward route to 2-oxazolidinones [J].

Arshadi, Sattar ;

Vessally, Esmail ;

Sobati, Marjan ;

Hosseinian, Akram ;

Bekhradnia, Ahmedreza .

JOURNAL OF CO2 UTILIZATION, 2017, 19 :120-129

[4] Novel (Hetero)arylalkenyl propargylamine compounds are protective in toxin-induced models of Parkinson's disease [J].

Baranyi, Maria ;

Porceddu, Pier Francesca ;

Goeloencser, Flora ;

Kulcsar, Szabina ;

Otrokocsi, Lilla ;

Kittel, Agnes ;

Pinna, Annalisa ;

Frau, Lucia ;

Huleatt, Paul B. ;

Khoo, Mui-Ling ;

Chai, Christina L. L. ;

Dunkel, Petra ;

Matyus, Peter ;

Morelli, Micaela ;

Sperlagh, Beata .

MOLECULAR NEURODEGENERATION, 2016, 11

[5] Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3-Csp) of Natural α-Amino Acids and Alkynes [J].

Bi, Hai-Peng ;

Teng, Qingfeng ;

Guan, Min ;

Chen, Wen-Wen ;

Liang, Yong-Min ;

Yao, Xiaojun ;

Li, Chao-Jun .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :783-788

[6] Zinc-Catalyzed Domino Hydroamination-Alkyne Addition [J].

Biyikal, Mustafa ;

Porta, Marta ;

Roesky, Peter W. ;

Blechert, Siegfried .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :1870-1875

[7] Propargylamine-derived multitarget-directed ligands: fighting Alzheimer's disease with monoamine oxidase inhibitors [J].

Bolea, Irene ;

Gella, Alejandro ;

Unzeta, Mercedes .

JOURNAL OF NEURAL TRANSMISSION, 2013, 120 (06) :893-902

[8] Aerobic Oxidative Homo- and Cross-Coupling of Amines Catalyzed by Phenazine Radical Cations [J].

Brisar, Rok ;

Unglaube, Felix ;

Hollmann, Dirk ;

Jiao, Haijun ;

Mejia, Esteban .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13481-13490

[9] Copper(II) catalyzed domino synthesis of quinoline derivatives from arylamines and alkynes [J].

Dai, Huimin ;

Li, Chun-Xiao ;

Yu, Chao ;

Wang, Zihao ;

Yan, Hong ;

Lu, Changsheng .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10) :2008-2011

[10] A Metal-Free Approach Toward Saturated N-Propargyl Heterocycles via an Annulation/Decarboxylative Coupling Sequence [J].

Feng, Huangdi ;

Jia, Huihui ;

Sun, Zhihua .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) :2447-2452

← 1 2 3 4 5 6 →