Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(I) bis-metal sequential catalysis

被引:105
作者
Huang, Pei-Qiang [1 ,2 ,3 ]
Ou, Wei [1 ,2 ]
Han, Feng [1 ,2 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, iChEM Collaborat Innovat Ctr Chem Energy Mat, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, iChEM Collaborat Innovat Ctr Chem Energy Mat, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY ENANTIOSELECTIVE CONSTRUCTION; C-H ACTIVATION; SECONDARY AMIDES; NUCLEOPHILIC-ADDITION; GRIGNARD-REAGENTS; TERMINAL ALKYNES; ORGANOMETALLIC REAGENTS; DIRECT TRANSFORMATION; LITHIUM ACETYLIDES; MAGNESIUM REAGENTS;
D O I
10.1039/c6cc05318a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation-Cu(I)-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the alkyne coupling partner. The method is general for tert-amides with or without alpha-hydrogen.
引用
收藏
页码:11967 / 11970
页数:4
相关论文
共 70 条
[1]   Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group [J].
Aschwanden, Patrick ;
Stephenson, Corey R. J. ;
Carreira, Erick M. .
ORGANIC LETTERS, 2006, 8 (11) :2437-2440
[2]  
Bechara WS, 2012, NAT CHEM, V4, P228, DOI [10.1038/NCHEM.1268, 10.1038/nchem.1268]
[3]   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
[4]   Selective Ruthenium-Catalyzed Reductive Alkoxylation and Amination of Cyclic Imides [J].
Cabrero-Antonino, Jose R. ;
Sorribes, Ivan ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) :387-391
[5]   Total synthesis of (±)-maistemonine and (±)-stemonamide [J].
Chen, Zhi-Hua ;
Zhang, Yong-Qiang ;
Chen, Zhi-Min ;
Tu, Yong-Qiang ;
Zhang, Fu-Min .
CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1836-1838
[6]   Total Synthesis of Gelsemoxonine through a Spirocyclopropane Isoxazolidine Ring Contraction [J].
Diethelm, Stefan ;
Carreira, Erick M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) :6084-6096
[7]   Diaminophosphine Oxide Ligand Enabled Asymmetric Nickel-Catalyzed Hydrocarbamoylations of Alkenes [J].
Donets, Pavel A. ;
Cramer, Nicolai .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11772-11775
[8]   An easily removable stereo-dictating group for enantioselective synthesis of propargylic amines [J].
Fan, Wu ;
Ma, Shengming .
CHEMICAL COMMUNICATIONS, 2013, 49 (86) :10175-10177
[9]   Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex [J].
Fischer, C ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (26) :4319-4321
[10]   Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines [J].
Gommermann, N ;
Koradin, X ;
Polborn, K ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5763-5766