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
  • [1] Nickel-Catalyzed Alkylation of Oxindoles with Secondary Alcohols
    Bera, Atanu
    Ghosh, Adrija
    Banerjee, Debasis
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7162 - 7171
  • [2] Nickel-catalyzed α-alkylation of ketones with benzyl alcohols
    Wu, Di
    Wang, Yubin
    Li, Min
    Shi, Lei
    Liu, Jichang
    Liu, Ning
    APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (02)
  • [3] Nickel-catalyzed alkylation of ketones and nitriles with primary alcohols
    Genc, Sertac
    Arslan, Burcu
    Gulcemal, Derya
    Gulcemal, Suleyman
    Gunnaz, Salih
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (48) : 9753 - 9762
  • [4] STEREOCHEMICAL ASPECTS OF THE NICKEL-CATALYZED ALKYLATION OF ALLYLIC ALCOHOLS
    CONSIGLIO, G
    MORANDINI, F
    PICCOLO, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) : 1846 - 1847
  • [5] NICKEL-CATALYZED ASYMMETRIC ALKYLATION OF SOME CHIRAL AND ACHIRAL ALLYLIC ALCOHOLS
    CONSIGLIO, G
    MORANDINI, F
    PICCOLO, O
    HELVETICA CHIMICA ACTA, 1980, 63 (04) : 987 - 989
  • [6] Nickel-Catalyzed Alkylation or Reduction of Allylic Alcohols with Alkyl Grignard Reagents
    Yang, Bo
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07): : 4772 - 4784
  • [7] NICKEL-CATALYZED SYNTHESIS OF ARYLACETONITRILES FROM ARYLZINC CHLORIDES AND BROMOACETONITRILE
    FREJD, T
    KLINGSTEDT, T
    SYNTHESIS-STUTTGART, 1987, (01): : 40 - 42
  • [8] Nickel-Catalyzed Phosphine Free Direct N-Alkylation of Amides with Alcohols
    Das, Jagadish
    Banerjee, Debasis
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06): : 3378 - 3384
  • [9] An Efficient and Selective Nickel-Catalyzed Direct N-Alkylation of Anilines with Alcohols
    Vellakkaran, Mani
    Singh, Khushboo
    Banerjee, Debasis
    ACS CATALYSIS, 2017, 7 (12): : 8152 - 8158
  • [10] Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
    Ngamnithiporn, Aurapat
    Jette, Carina I.
    Bachman, Shoshana
    Virgil, Scott C.
    Stoltz, Brian M.
    CHEMICAL SCIENCE, 2018, 9 (09) : 2547 - 2551