Nickel/Titanocene-Catalyzed Electrophilic Acylation Coupling of Styrene Oxides

被引：3
|
作者：
Li, Jincan [1 ]
Cao, Chang [1 ]
Wu, Haihong [1 ]
Dong, Kaiwu [2 ]
机构：
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] East China Normal Univ, Shanghai Frontiers Sci Ctr Mol Intelligent Synthe, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 38期
关键词：
C(SP(3))-H BONDS; KETONE SYNTHESIS; ALKYL-HALIDES; ARYL HALIDES; NICKEL; CARBOACYLATION; ANHYDRIDES; EPOXIDES; ACIDS; MILD;
D O I：
10.1021/acs.orglett.3c02402
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cross-coupling of epoxides with acyl chlorides or anhydrides by a nickel/titanocene dual catalytic system is established. A variety of synthetically useful beta-hydroxy ketones were obtained in good to high yields by using modified pyridine-oxazoline ligand. The reaction proceeds via the cooperation of titanocene-catalyzed ring-opening of epoxides and nickel-catalyzed acylation of the benzylic radical intermediate.
引用
收藏
页码：6959 / 6963
页数：5
相关论文
共 50 条
  • [31] Homogeneous, titanocene-catalyzed dehydrocoupling of amine-borane adducts
    Clark, Timothy J.
    Russell, Christopher A.
    Manners, Ian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) : 9582 - 9583
  • [32] Titanocene-Catalyzed Radical Opening of N-Acylated Aziridines
    Zhang, Yong-Qiang
    Vogelsang, Elisabeth
    Qu, Zheng-Wang
    Grimme, Stefan
    Gansaeuer, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) : 12654 - 12657
  • [33] A titanocene-catalyzed intramolecular ene reaction: Cycloisomerization of enynes and dienynes
    Sturla, SJ
    Kablaoui, NM
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1976 - 1977
  • [34] Titanocene-Catalyzed Alkylation of Aryl-Substituted Alkenes with Alkyl Halides
    Kambe, N. (kambe@chem.eng.osaka-u.ac.jp), 1600, Chemical Society of Japan (76):
  • [35] Scope of the intramolecular titanocene-catalyzed Pauson-Khand type reaction
    Hicks, FA
    Kablaoui, NM
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) : 5881 - 5898
  • [36] Titanocene-catalyzed double silylation of dienes and aryl alkenes with chlorosilanes
    Terao, J
    Kambe, N
    Sonoda, N
    TETRAHEDRON LETTERS, 1998, 39 (52) : 9697 - 9698
  • [37] The titanocene-catalyzed reduction of acetamides to tertiary amines by PhMeSiH2
    Selvakumar, K
    Rangareddy, K
    Harrod, JF
    CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (08) : 1244 - 1248
  • [38] Titanocene-catalyzed alkylation of aryl-substituted alkenes with alkyl halides
    Terao, J
    Watabe, H
    Miyamoto, M
    Kambe, N
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (11) : 2209 - 2214
  • [39] Titanocene-catalyzed carbosilylation of alkenes and dienes using alkyl halides and chlorosilanes
    Nii, S
    Terao, J
    Kambe, N
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17): : 5291 - 5297
  • [40] Titanocene-catalyzed reductive epoxide opening:: The quest for novel hydrogen atom donors
    Gansäuer, A
    Barchuk, A
    Fielenbach, D
    SYNTHESIS-STUTTGART, 2004, (15): : 2567 - 2573
12345