Organophosphate-accelerated copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross couplings

被引：8
|
作者：
Xu, Wei [1 ]
Yu, Bo [1 ]
Sun, Huaming [1 ]
Zhang, Guofang [1 ]
Zhang, Weiqiang [1 ]
Gao, Ziwei [1 ]
机构：
[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Key Lab Appl Surface & Colloid Chem, Minist Educ, Xian, Peoples R China
来源：
APPLIED ORGANOMETALLIC CHEMISTRY | 2015年 / 29卷 / 05期
基金：
中国国家自然科学基金; 国家教育部博士点专项基金资助;
关键词：
Sonogashira coupling; organophosphate; Cu(II) complexes; TERMINAL ALKYNES; ARYL HALIDES; LIGAND-FREE; PALLADIUM-FREE; DIARYL ETHERS; VINYL IODIDES; ARYLATION; CYCLOADDITION; LOADINGS;
D O I：
10.1002/aoc.3291
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A dramatic acceleration in copper-catalyzed Sonogashira-type reactions was observed when an organophosphate was used as additive. The catalyst systems featuring low copper loading (0.5 mol% < Cu < 5 mol%) gave Sonogashira-type products with a broad scope of aromatic and aliphatic terminal alkynes as well as aryl iodides in good to excellent yields. Among the organophosphate/copper catalytic systems, that of 4 mol% Cu(OTf)(2)/10 mol% (R)-(-)-1,1-binaphthyl-2,2-diyl hydrogenphosphate exhibited the highest catalytic activity. Copyright (c) 2015 John Wiley & Sons, Ltd.
引用
收藏
页码：301 / 304
页数：4
相关论文
共 50 条
  • [21] Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)-H Bonds of Benzamides
    Chabrier, Amelie
    Bruneau, Alexandre
    Benmahdjoub, Sara
    Benmerad, Belkacem
    Belaid, Sabrina
    Brion, Jean-Daniel
    Alami, Mouad
    Messaoudi, Samir
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) : 15006 - 15010
  • [22] Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids
    Zhao, Sheng
    Chen, Fa-Jie
    Liu, Bin
    Shi, Bing-Feng
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1302 - 1309
  • [23] Copper-Catalyzed Direct Acyloxylation of C(sp2)-H Bonds in Aromatic Amides
    Wang, Feifan
    Hu, Qiyan
    Shu, Chao
    Lin, Zhiyang
    Min, Dewen
    Shi, Tianchao
    Zhang, Wu
    ORGANIC LETTERS, 2017, 19 (13) : 3636 - 3639
  • [24] Copper-Catalyzed Site-Selective C(sp2)-H Alkynylation of Allenes
    Duan, Xiu
    Jin, Qihao
    Wang, Kaifeng
    Sun, Yifan
    Wei, Youhao
    Wang, Zheng
    Qiu, Jiang-Kai
    Guo, Kai
    Bao, Xiaoguang
    Wu, Xinxin
    ACS CATALYSIS, 2024, 14 (17): : 13219 - 13226
  • [25] Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds
    Li, Yaqiong
    Fan, Yuhang
    Jia, Qianfa
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 350 - 362
  • [26] Synthesis of α-Quaternary β-Lactams via Copper-Catalyzed Enantioconvergent Radical C(sp3)-C(sp2) Cross-Coupling with Organoboronate Esters
    Wang, Fu-Li
    Liu, Lin
    Yang, Chang-Jiang
    Luan, Cheng
    Yang, Jing
    Chen, Ji-Jun
    Gu, Qiang-Shuai
    Li, Zhong-Liang
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)
  • [27] Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization
    Zhu, Da-Liang
    Xu, Ruijie
    Wu, Qi
    Li, Hai-Yan
    Lang, Jian-Ping
    Li, Hong-Xi
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14): : 9201 - 9212
  • [28] Copper-Catalyzed Sequential C(sp2)/C(sp3)-H Amination of 2-Vinylanilines with N-Fluorobenzenesulfonimide
    Cao, Wen-Bin
    Xu, Xiao-Ping
    Ji, Shun-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) : 1771 - 1776
  • [29] Ni-catalyzed C(sp2)-carbon and C(sp2)-heteroatom cross-coupling reactions
    Li, Z
    Fu, Y
    Liu, L
    Guo, QX
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (12) : 1508 - 1529
  • [30] Copper-Catalyzed Enaminone C(sp2)-N Bond Phosphonation for Stereoselective Synthesis of Alkenylphosphonates
    Liu, Ting
    Wei, Li
    Zhao, Baoli
    Liu, Yunyun
    Wan, Jie-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9861 - 9868
12345