Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes

被引：3
|
作者：
Zeng, Hui-Hui [1 ]
Wang, Yu-Qing [1 ]
He, Yong-Yu [1 ]
Zhong, Xiao-Ling [1 ]
Li, Hongguang [1 ,2 ]
Ma, Ai-Jun [1 ]
Peng, Jin-Bao [1 ]
机构：
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China
[2] Wuyi Univ, Guangdong Prov Key Lab Large Anim Models Biomed, Jiangmen 529020, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 04期
关键词：
CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE ARYLBORATION; STEREOSELECTIVE-SYNTHESIS; BORONIC ACIDS; IN-SITU; BOROACYLATION; AMINOBORATION; ALLENES; BIS(PINACOLATO)DIBORON; CARBOBORATION;
D O I：
10.1021/acs.joc.3c02670
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu/Pd-cocatalyzed 1,5-boroacylation of cyclopropyl-substituted ACPs with B2pin2 and acid chlorides has been developed. Using cyclopropyl-substituted ACPs as the starting material, a broad range of 1,5-boroacylated products with multiple functional groups was prepared in good yields with excellent regio- and stereoselectively. Both aromatic and aliphatic acid chlorides were tolerated in this reaction.
引用
收藏
页码：2637 / 2648
页数：12
相关论文
共 50 条
  • [21] Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes
    Liu, Jiawang
    Yang, Ji
    Baumann, Wolfgang
    Jackstell, Ralf
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (31) : 10683 - 10687
  • [22] Pd-catalyzed exclusively regioselective [5+4] cycloaddition for the construction of 1,5-di/ox-azonanes
    Liu, Wenqi
    Zang, Meng
    Zhang, Jian
    Wang, Quannan
    Liu, Yang-Zi
    Deng, Wei-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (07) : 1680 - 1685
  • [23] Preparation of 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine via Pd-catalyzed Cyclization
    Singer, RA
    McKinley, JD
    Barbe, G
    Farlow, RA
    ORGANIC LETTERS, 2004, 6 (14) : 2357 - 2360
  • [24] Synthesis of 2-Substituted Indoles by Pd-Catalyzed Reductive Cyclization of 1-Halo-2-nitrobenzene with Alkynes
    Lokolkar, Manjunath S.
    Mane, Pravin A.
    Dey, Sandip
    Bhanage, Bhalchandra M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (05)
  • [25] Recent advances in photoinitiated Pd-catalyzed desaturation and Heck-type reactions via 1,5-hydrogen atom transfer
    Tang, Lu-ning
    Miao, Jia-cheng
    Chen, Ming
    CHEMICAL COMMUNICATIONS, 2025, 61 (24) : 4621 - 4629
  • [26] New Pd-catalyzed allyl-allyl cross-coupling method: Enantioselective synthesis of branched 1,5-dienes
    Le, Hai
    Kyne, Robert E.
    Brozek, Laura
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [27] Cu/Pd-catalyzed arylboration of a 1-silyl-1,3-cyclohexadiene for stereocontrolled and diverse cyclohexane/ene synthesis
    Crook, Phillip F.
    Lear, Alan R.
    Das, Suman
    Brown, M. Kevin
    CHEMICAL SCIENCE, 2023, 14 (38) : 10467 - 10470
  • [28] Synthesis of gem-Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes
    Xu, Wen-Yan
    Li, Yu-Jie
    Gong, Tian-Jun
    Fu, Yao
    ORGANIC LETTERS, 2022, 24 (32) : 5884 - 5889
  • [29] Regioselective Synthesis of 2,4-Substituted Pyrido[1,2:1,5]pyrazolo[3,4-d]pyrimidines through Sequential Pd-Catalyzed Arylation and SNAr Reactions
    Belaroussi, Rabia
    El Hakmaoui, Ahmed
    Akssira, Mohamed
    Guillaumet, Gerald
    Routier, Sylvain
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) : 3550 - 3558
  • [30] Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes
    Olivares, Astrid M.
    Weix, Daniel J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (07) : 2446 - 2449
12345