Redox-Neutral Nickel-Catalyzed Cross-Coupling Reactions of (Homo)allylic Alcohols and Aryltriflates

被引:20
|
作者
Wang, Xuchao [1 ,2 ]
Liu, Feipeng [1 ,2 ]
Yan, Zijuan [1 ,2 ]
Qiang, Qing [1 ,2 ]
Huang, Wei [1 ,2 ]
Rong, Zi-Qiang [1 ,2 ]
机构
[1] Northwestern Polytech Univ, Frontiers Sci Ctr Flexible Elect FSCFE, Shaanxi Inst Flexible Elect SIFE, Xian 710072, Peoples R China
[2] Northwestern Polytech Univ, Shaanxi Inst Biomed Mat & Engn SIBME, Xian 710072, Peoples R China
来源
ACS CATALYSIS | 2021年 / 11卷 / 12期
基金
中国国家自然科学基金;
关键词
nickel catalysis; isomerization; ketone; cross-coupling; redox-neutral transformation; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE ISOMERIZATION; ASYMMETRIC ISOMERIZATION; ALDEHYDES; KETONES;
D O I
10.1021/acscatal.1c00951
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Herein, we report a redox-neutral Ni-catalyzed cross-coupling reaction of two readily available precursors to produce the corresponding ketones that are an important structural motif in numerous biologically active entities. By the use of a commercially available nickel/Triphos catalytic system, a range of easily accessible alkenyl primary alcohols and aryltriflates can be converted in a rapidly assembled fashion to valuable ketones with good yields and wide functional group tolerance. We also demonstrate the utility of this transformation by late-stage functionalization of a large set of complex molecules with good efficiency, which offers a distinct entry to more functionalized aromatic ketones.
引用
收藏
页码:7319 / 7326
页数:8
相关论文
共 50 条
  • [21] ARYL MESYLATES IN METAL-CATALYZED HOMO-COUPLING AND CROSS-COUPLING REACTIONS .4. SCOPE AND LIMITATIONS OF ARYL MESYLATES IN NICKEL-CATALYZED CROSS-COUPLING REACTIONS
    PERCEC, V
    BAE, JY
    HILL, DH
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21): : 6895 - 6903
  • [22] Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols
    Verheyen, Thomas
    Van Turnhout, Lars
    Vandavasi, Jaya Kishore
    Isbrandt, Eric S.
    De Borggraeve, Wim M.
    Newman, Stephen G.
    Journal of the American Chemical Society, 2019,
  • [23] Nickel-Catalyzed Reductive Cross-Coupling of α-Trifluoromethylated Alkyl Electrophiles and Allylic Sulfones
    Xu, Qiao-Lin
    Zhao, Yi
    Liu, Xia-Ling
    Jin, Na
    He, Ke-Han
    Pan, Fei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [24] Synthesis of 1,4-enynes via nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents
    He, Xue-Yi
    Wang, Zhong-Xia
    CHEMICAL COMMUNICATIONS, 2021, 57 (90) : 11988 - 11991
  • [25] Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling
    Hofstra, Julie L.
    Cherney, Alan H.
    Ordner, Ciara M.
    Reisman, Sarah E.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 139 - 142
  • [26] Cross-coupling reactions of allylic alcohols in water
    Manabe, K
    Nakada, K
    Aoyama, N
    Kobayashi, S
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1499 - 1503
  • [27] Nickel-Catalyzed Cross-Electrophile Coupling Reactions of Alcohols and Their Derivatives
    Jana, Sayan K.
    Maji, Biplab
    SYNTHESIS-STUTTGART, 2025,
  • [28] Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
    Wang, Gaonan
    Gan, Yi
    Liu, Yuanhong
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (10) : 916 - 920
  • [29] Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
    Li, Zijian
    Sun, Wenxuan
    Wang, Xianxu
    Li, Luyang
    Zhang, Yong
    Li, Chao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (09) : 3536 - 3543
  • [30] Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents
    Yang, Bo
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09): : 4542 - 4549