Palladium-Catalyzed Three-Component Tandem Reaction for One-pot Highly Stereoselective Synthesis of (Z)-α-Hydroxymethyl Allylic Sulfones

被引:26
|
作者
Hou, Yunlei [1 ]
Shen, Qi [1 ]
Li, Zefei [1 ]
Chen, Shaowei [1 ]
Zhao, Yanfang [1 ]
Qin, Mingze [1 ]
Gong, Ping [1 ]
机构
[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Liaoning, Peoples R China
关键词
allylic sulfones; three-component tandem reaction; Pd-catalyzed; sulfonyl hydrazides; allenes; C-H AMINATION; ARYL IODIDES; ALLENYLBORONATE PLATFORM; ORGANIC-SYNTHESIS; ALLYLATION; ALLENES; HYDRAZIDES; ALCOHOLS; AMINES; SULFONYLATION;
D O I
10.1002/adsc.201701011
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel method is reported for the stereoselective synthesis of highly functionalized allyl aryl sulfones. This protocol is based on a Pd-catalyzed three-component tandem reaction of sulfonyl hydrazides and aryl iodides with allenes and exhibits high (Z)-selectivity, good yields, minimal waste, ample product scope, and operational simplicity.
引用
收藏
页码:631 / 636
页数:6
相关论文
共 50 条
  • [41] One-pot synthesis of substituted quinolines by iridium-catalyzed three-component coupling reaction
    Igarashi, T
    Inada, T
    Sekioka, T
    Nakajima, T
    Shimizu, I
    CHEMISTRY LETTERS, 2005, 34 (01) : 106 - 107
  • [42] Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction
    Gommermann, Nina
    Knochel, Paul
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4380 - 4392
  • [43] L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones
    Dodda, Rajasekhar
    Zhao, Cong-Gui
    SYNTHESIS-STUTTGART, 2006, 19 (19): : 3238 - 3242
  • [44] One-Pot Stereoselective Synthesis of (Z)-1,2-Disubstituted Vinyl Sulfones by Hydrostannylation-Stille Tandem Reaction of Acetylenic Sulfones
    Chen, Guiqin
    Yu, Yan
    Cai, Mingzhong
    SYNTHETIC COMMUNICATIONS, 2009, 39 (08) : 1478 - 1487
  • [45] Palladium-catalyzed oxidative three-component tandem annulation reaction: Access to polysubstituted pyrroles
    Bashkar, Mohammad
    Nowrouzi, Najmeh
    MOLECULAR CATALYSIS, 2024, 562
  • [46] Highly efficient one-pot three-component Mannich reaction catalyzed by ZnO-nanoparticles in water
    MaGee, David Ian
    Dabiri, Minoo
    Salehi, Peyman
    Torkian, Laleh
    ARKIVOC, 2011, : 156 - 164
  • [47] An efficient and ecofriendly synthesis of highly functionalized pyridones via a one-pot three-component reaction
    Hosseini, Hajar
    Bayat, Mohammad
    RSC ADVANCES, 2018, 8 (48) : 27131 - 27143
  • [48] Synthesis of Trifluoromethylated Pyrroles via a One-Pot Three-Component Reaction
    Rahmani, Fariba
    Darehkordi, Ali
    SYNLETT, 2017, 28 (10) : 1224 - 1226
  • [49] Novel One-Pot Three-Component Reaction for the Synthesis of Functionalized Spiroquinazolinones
    Tajbakhsh, Mahdieh
    Ramezanpour, Sorour
    Balalaie, Saeed
    Bijanzadeh, Hamid Reza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (05) : 1559 - 1564
  • [50] One-pot three-component Mannich reaction catalyzed by 2-hydroxylpyridine
    Jin Li-li
    Lei Yun-tao
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2013, 29 (04) : 710 - 713