Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

被引:2
|
作者
Kalinin, Dmitrii [1 ,2 ]
Ulven, Trond [1 ,3 ]
机构
[1] Univ Southern Denmark, Dept Phys Chem & Pharm, DK-5230 Odense, Denmark
[2] Univ Munster, Inst Pharmaceut & Med Chem, D-48149 Munster, Germany
[3] Univ Copenhagen, Dept Drug Design & Pharmacol, DK-2100 Copenhagen, Denmark
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期
关键词
UNSYMMETRICAL KETONE SYNTHESIS; UNACTIVATED ALKYL BROMIDES; ORGANOZINC REAGENTS; CONVENIENT SYNTHESIS; ORGANIC HALIDES; CROSS-COUPLINGS; EMPETRUM-NIGRUM; FLUORIDE-ION; PALLADIUM; ZINC;
D O I
10.1021/acs.joc.3c00948
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)-aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C-(sp3)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.
引用
收藏
页码:16633 / 16638
页数:6
相关论文
共 50 条
  • [21] A useful Pd-catalyzed Negishi coupling approach to benzylic sulfonamide derivatives
    Zhou, Gang
    Ting, Pauline
    Aslanian, Robert
    Piwinski, John J.
    ORGANIC LETTERS, 2008, 10 (12) : 2517 - 2520
  • [22] Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles
    Feng, Xiujuan
    Song, Jiliang
    Bao, Ming
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2018, 65 (03) : 337 - 345
  • [23] Pd-catalyzed Negishi coupling of pyrazole triflates with alkyl zinc halides
    Zhang, Ting
    Gao, Xiaodi
    Wood, Harold B.
    TETRAHEDRON LETTERS, 2011, 52 (02) : 311 - 313
  • [24] Functional-Group-Tolerant Catalytic Migratory Oxidative Coupling of Nitrones
    Hashizume, Shogo
    Oisaki, Kounosuke
    Kanai, Motomu
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (11) : 2600 - 2606
  • [25] Synthesis of Benzoylacetonitriles from Pd-Catalyzed Carbonylation of Aryl Iodides and Trimethylsilylacetonitrile
    Park, Ahbyeol
    Lee, Sunwoo
    ORGANIC LETTERS, 2012, 14 (04) : 1118 - 1121
  • [26] Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
    Lian, Zhong
    Yin, Hongfei
    Friis, Stig D.
    Skrydstrup, Troels
    CHEMICAL COMMUNICATIONS, 2015, 51 (37) : 7831 - 7834
  • [27] Pd-catalyzed coupling of β-hydroxy α-diazocarbonyl compounds with aryl iodides: a migratory insertion/β-hydroxy elimination sequence
    Zhou, Lei
    Liu, Yizhou
    Zhang, Yan
    Wang, Jianbo
    CHEMICAL COMMUNICATIONS, 2011, 47 (12) : 3622 - 3624
  • [28] Pd/Cu-Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem-Difluoroalkenes: Efficient Synthesis of α-Fluorochalcones
    Wu, Fu-Peng
    Yuan, Yang
    Liu, Jiawang
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (16) : 8818 - 8822
  • [29] Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC
    Cui, Yanli
    Guo, Xiaoning
    Wang, Yingyong
    Guo, Xiangyun
    CHINESE JOURNAL OF CATALYSIS, 2015, 36 (03) : 322 - 327
  • [30] Pd-Catalyzed Negishi Cross-Coupling of Vinyl Bromides with Diborylmethylzinc Chloride
    Kim, Minjae
    Lee, Jun Hee
    Cho, Seung Hwan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (03) : 499 - 501