Synthesis of Heterobenzyl Sulfoxides Enabled by Palladium- Catalyzed Allylic Alkylation of Sulfenate Anions with Allenamides

被引:6
|
作者
Wang, Lei [1 ]
Wu, Shuaijie [1 ]
Zhang, Shuting [1 ]
Hu, Qianqian [1 ]
Wang, Qiang [1 ]
Sun, Jing [1 ]
Han, Ying [1 ]
Yan, Chao-Guo [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 21期
基金
中国国家自然科学基金;
关键词
ARYL BENZYL SULFOXIDES; ENANTIOSELECTIVE ARYLATION; ASYMMETRIC-SYNTHESIS; PUMMERER REACTION; GENERATION; INHIBITORS; DISCOVERY; OXIDATION; CASCADES; STRATEGY;
D O I
10.1021/acs.joc.2c01998
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient palladium-catalyzed allenamide allylic alkylation of sulfenate anions under mild conditions is demonstrated. The present methodology provides a practical protocol to access various sulfoxide-containing heterocyclic compounds. The salient features of this transformation include a broad substrate scope, good functional group tolerance, easy to scale-up, and ready synthetic transformation.
引用
收藏
页码:14646 / 14656
页数:11
相关论文
共 50 条
  • [21] New chiral phosphetanes: Synthesis and use in the palladium-catalyzed allylic alkylation
    Marinetti, A
    Kruger, V
    Ricard, L
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) : 465 - 472
  • [22] PALLADIUM-CATALYZED ALLYLIC ALKYLATION OF ALLYLIC NITROCOMPOUNDS WITH STABILIZED CARBANIONS
    ONO, N
    HAMAMOTO, I
    KAJI, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1439 - 1443
  • [23] Sulfoxides derived from Cinchona alkaloids-chiral ligands in palladium-catalyzed asymmetric allylic alkylation
    Wojaczynska, Elzbieta
    Zielinska-Blajet, Mariola
    Turowska-Tyrk, Ilona
    Skarzewski, Jacek
    TETRAHEDRON-ASYMMETRY, 2010, 21 (07) : 853 - 858
  • [24] Enantio- and regiocontrol in palladium- and tungsten-catalyzed allylic substitutions
    Pretot, R
    Lloyd-Jones, GC
    Pfaltz, A
    PURE AND APPLIED CHEMISTRY, 1998, 70 (05) : 1035 - 1040
  • [25] A case for enantioselective allylic alkylation catalyzed by palladium nanoparticles
    Jansat, S
    Gómez, M
    Philippot, K
    Muller, G
    Guiu, E
    Claver, C
    Castillón, S
    Chaudret, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) : 1592 - 1593
  • [26] Diastereodivergent Processes in Palladium-Catalyzed Allylic Alkylation
    Oliveira, Maria Teresa
    Audisio, Davide
    Niyomchon, Supaporn
    Maulide, Nuno
    CHEMCATCHEM, 2013, 5 (06) : 1239 - 1247
  • [27] Palladium(0)-catalyzed intramolecular allylic alkylation of diketoesters
    Atesin, Tulay
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [28] PALLADIUM(0)-CATALYZED ALLYLIC ALKYLATION AND AMINATION OF ALLYLNITROALKANES
    TAMURA, R
    HEGEDUS, LS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3727 - 3729
  • [29] Palladium-catalyzed asymmetric allylic alkylation with an indenide
    Hayashi, T
    Suzuka, T
    Okada, A
    Kawatsura, M
    TETRAHEDRON-ASYMMETRY, 2004, 15 (03) : 545 - 548
  • [30] Control of the Regioselectivity in Palladium(0)-Catalyzed Allylic Alkylation
    Norsikian, Stephanie
    Chang, Chih-Wei
    CURRENT ORGANIC SYNTHESIS, 2009, 6 (03) : 264 - 289