Nickel-Catalyzed ?-Alkylation of Arylacetonitriles with Challenging Alcohols br

被引:9
|
作者
Saha, Ratnakar [1 ]
Panda, Surajit [1 ]
Nanda, Amareshwar [1 ]
Bagh, Bidraha [1 ]
机构
[1] OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res NISER, Sch Chem Sci, Bhubaneswar 752050, Odisha, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 10期
关键词
METAL-LIGAND COOPERATION; DIRECT N-ALKYLATION; ALPHA-ALKYLATION; TRANSITION-METAL; SECONDARY ALCOHOLS; MOLECULAR CATALYSTS; RUTHENIUM COMPLEXES; HYDROGEN-TRANSFER; C-ALKYLATION; NITRILES;
D O I
10.1021/acs.joc.2c02026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nickel(II) complex 1 was utilized as a sustainable catalyst for alpha-alkylation of arylacetonitriles with challenging secondary alcohols. Arylacetonitriles with a wide range of functional groups were tolerated, and various cyclic and acyclic secondary alcohols were utilized to yield a large number of alpha- alkylated products. The plausible mechanism involves the base promoted activation of precatalyst 1 to an active catalyst 2 (dehydrochlorinated product) which activates the O-H and C-H bonds of the secondary alcohol in a dehydrogenative pathway.
引用
收藏
页码:6664 / 6676
页数:13
相关论文
共 50 条
  • [21] Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes
    Zhenkang Ai
    Hui Chen
    Xuebin Liao
    Chinese Chemical Letters, 2025, 36 (03) : 281 - 286
  • [22] Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy
    Hu, Miao
    Jiang, Yong
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    Hu, Xinquan
    Jin, Liqun
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (22) : 10057 - 10062
  • [23] Nickel-catalyzed hydrogen-borrowing strategy: chemo-selective alkylation of nitriles with alcohols
    Bera, Sourajit
    Bera, Atanu
    Banerjee, Debasis
    CHEMICAL COMMUNICATIONS, 2020, 56 (50) : 6850 - 6853
  • [24] Nickel-Catalyzed Sustainable and Selective Alkylation of Alcohols to α-Alkylated Ketones via Borrowing Hydrogen Approach
    Chakraborty, Gargi
    Pal, Subhasree
    Chakraborty, Subhajit
    Paul, Nanda D.
    SYNLETT, 2023, 34 (06) : 635 - 644
  • [25] Nickel-Catalyzed Chemoselective Arylation of Amino Alcohols
    Morrison, Kathleen M.
    Yeung, Charles S.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [26] NICKEL-CATALYZED REGIOSELECTIVE ALLYLATION OF ALLYLIC ALCOHOLS
    YANAGISAWA, A
    NOMURA, N
    HABAUE, S
    YAMAMOTO, H
    TETRAHEDRON LETTERS, 1989, 30 (46) : 6409 - 6412
  • [27] Mechanistic Investigation of the Nickel-Catalyzed Carbonylation of Alcohols
    Sabater, Sara
    Menche, Maximilian
    Ghosh, Tamal
    Krieg, Saskia
    Rueck, Katharina S. L.
    Paciello, Rocco
    Schaefer, Ansgar
    Comba, Peter
    Hashmi, A. Stephen K.
    Schaub, Thomas
    ORGANOMETALLICS, 2020, 39 (06) : 870 - 880
  • [28] Nickel-Catalyzed Reductive Hydrolysis of Nitriles to Alcohols
    Kuloor, Chakreshwara
    Goyal, Vishakha
    Zboril, Radek
    Beller, Mathias
    Jagadeesh, Rajenahally V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (10)
  • [29] Nickel-catalyzed arylative substitution of homoallylic alcohols
    Tran, Hai N.
    Nguyen, Chau M.
    Koeritz, Mason T.
    Youmans, Dustin D.
    Stanley, Levi M.
    CHEMICAL SCIENCE, 2022, 13 (39) : 11607 - 11613
  • [30] Nickel-catalyzed esterification of mandelic acids with alcohols
    Liu, Changhong
    Marhaba, Mamat
    Dilshat, Abdukerem
    Zhu, Wenli
    Xia, Kun
    Mao, Zechuan
    Ablimit, Abdukader
    ARABIAN JOURNAL OF CHEMISTRY, 2023, 16 (01)