Synthesis of Allenes via Gold-Catalyzed Intermolecular Reaction of Propargylic Alcohols and Aromatic Compounds

被引:40
作者
Xu, Cheng-Fu [1 ]
Xu, Mei [1 ]
Yang, Liu-Qing [1 ]
Li, Chuan-Ying [1 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 1,3-DISUBSTITUTED ALLENES; OLEFINATION; SUBSTITUTION; ALDEHYDES; INDOLES; COMPLEX; KETONES; ALKYNES;
D O I
10.1021/jo300147u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.
引用
收藏
页码:3010 / 3016
页数:7
相关论文
共 50 条
[21]   Gold-Catalyzed Synthesis of 2-Sulfenylspiroindolenines via Spirocyclizations [J].
Magne, Valentin ;
Retailleau, Pascal ;
Marinetti, Angela ;
Voituriez, Arnaud ;
Guinchard, Xavier .
MOLBANK, 2018, (01)
[22]   Gold-Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6-Enynes: Reactivity, Scope, and Mechanistic Aspects [J].
Schelwies, Mathias ;
Moser, Ralph ;
Dempwolff, Adrian L. ;
Rominger, Frank ;
Helmchen, Guenter .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) :10888-10900
[23]   Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers [J].
Boreux, Arnaud ;
Lonca, Geoffroy H. ;
Riant, Olivier ;
Gagosz, Fabien .
ORGANIC LETTERS, 2016, 18 (19) :5162-5165
[24]   Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol [J].
Liao, Shengrong ;
Porta, Alessio ;
Cheng, Xinpeng ;
Ma, Xu ;
Zanoni, Giuseppe ;
Zhang, Liming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) :8250-8254
[25]   Gold-Catalyzed Direct Intermolecular Coupling of Ketones, Secondary Amines, and Alkynes: A Facile and Versatile Access to Propargylic Amines Containing a Quaternary Carbon Center [J].
Cheng, Ming ;
Zhang, Qiang ;
Hu, Xiao-Yu ;
Li, Bo-Gang ;
Ji, Jian-Xin ;
Chan, Albert S. C. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1274-1278
[26]   Gold-catalyzed efficient preparation of linear α-haloenones from propargylic acetates [J].
Yu, Meng ;
Zhang, Guozhu ;
Zhang, Liming .
TETRAHEDRON, 2009, 65 (09) :1846-1855
[27]   Gold-Catalyzed Regiospecific Hydration of N-Tosyl Propargylic Amines [J].
Ying, Jun ;
Wang, Hai ;
Qi, Xinxin ;
Peng, Jin-Bao ;
Wu, Xiao-Feng .
ORGANOMETALLICS, 2018, 37 (17) :2837-2841
[28]   Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine [J].
Kinjo, Rei ;
Donnadieu, Bruno ;
Bertrand, Guy .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5560-5563
[29]   Synthesis of Carbonyl Compounds by Gold-Catalyzed Carbonylation Reactions [J].
Cao, Yanwei ;
He, Lin .
SYNLETT, 2022, 33 (11) :1003-1010
[30]   Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes: Simple and Efficient Synthesis of α-Mesyloxy Ketones [J].
Xie, Longyong ;
Liang, Zhiwu ;
Yan, Dong ;
He, Weimin ;
Xiang, Jiannan .
SYNLETT, 2013, 24 (14) :1809-1812