Regioselective Synthesis of 1,4-Dienes via Palladium-Catalyzed Oxidative Allylation of N-Tosylhydrazones

被引：2
|
作者：
Jin, Yangbin [1 ]
Li, Chunsheng [1 ]
Wu, Wanqing [1 ]
Jiang, Huanfeng [1 ]
机构：
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guang Dong Prov, Guangzhou 510641, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 14期
基金：
中国国家自然科学基金;
关键词：
allyl-Pd electrophile intermediate; olefination; skipped dienes; C-H ALKYLATION; CROSS-COUPLING REACTIONS; TERMINAL OLEFINS; SKIPPED DIENES; ASYMMETRIC HYDROVINYLATION; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATIONS; ALKENES; ROUTE; OXYGENATION;
D O I：
10.1002/adsc.202300319
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A palladium-catalyzed allylic C-H oxidative allylation of N-tosylhydrazones to synthesize skipped 1,4-dienes is demonstrated. This direct allylic alkylation reaction has excellent site selectivity, tolerates a wide range of functional groups, and affords 1,4-dienes in moderate to good yield. Moreover, this olefination method allows the regio- and stereoselective synthesis of 1,4-dienes containing a trisubstituted alkene. Preliminary mechanistic studies reveal that the reaction undergoes allylic C(sp(3))-H activation and a subsequent carbene migratory insertion.
引用
收藏
页码：2338 / 2343
页数：6
相关论文
共 50 条
  • [1] Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones
    Jiang, Huanfeng
    He, Li
    Li, Xianwei
    Chen, Huoji
    Wu, Wanqing
    Fu, Wei
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (80) : 9218 - 9220
  • [2] Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
    Zhou, Ping-Xin
    Luo, Jian-Yi
    Zhao, Lian-Biao
    Ye, Yu-Ying
    Liang, Yong-Min
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (31) : 3254 - 3256
  • [3] Synthesis of 1-bromo-1,4-dienes via palladium-catalyzed bromoallylation of allcynes
    Wen, Yanmei
    Jiang, Huanfeng
    [J]. TETRAHEDRON LETTERS, 2013, 54 (31) : 4034 - 4037
  • [4] Palladium-Catalyzed Oxidative CrossCoupling of N-Tosylhydrazones with Indoles: Synthesis of N-Vinylindoles
    Zeng, Xiaobao
    Cheng, Guolin
    Shen, Jinhai
    Cui, Xiuling
    [J]. ORGANIC LETTERS, 2013, 15 (12) : 3022 - 3025
  • [5] PALLADIUM-CATALYZED ARYLATION AND VINYLATION OF 1,4-DIENES
    BENDER, DD
    STAKEM, FG
    HECK, RF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07): : 1278 - 1284
  • [6] Palladium-Catalyzed Amidation of N-Tosylhydrazones with Isocyanides
    Zhou, Fengtao
    Ding, Ke
    Cai, Qian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (44) : 12268 - 12271
  • [7] Palladium-catalyzed allylation of alkynes with allyl alcohol in aqueous media: Highly regio and stereoselective synthesis of 1,4-dienes
    Huang, JM
    Zhou, L
    Jiang, HF
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) : 1945 - 1949
  • [8] Palladium-Catalyzed Alkylation of 1,4-Dienes by C?H Activation
    Trost, Barry M.
    Hansmann, Max M.
    Thaisrivongs, David A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4950 - 4953
  • [9] Palladium-Catalyzed Insertion of N-tosylhydrazones and Trapping with Carbon Nucleophiles
    Zhou, Ping-Xin
    Ye, Yu-Ying
    Liang, Yong-Min
    [J]. ORGANIC LETTERS, 2013, 15 (19) : 5080 - 5083
  • [10] Regioselective Synthesis of Naphtho-fused Heterocycles via Palladium(0)-Catalyzed Tandem Reaction of N-Tosylhydrazones
    Thang Ngoc Ngo
    Tuan Thanh Dang
    Villinger, Alexander
    Langer, Peter
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) : 1328 - 1336
12345