Nickel-catalyzed coupling reactions of alkenes

被引:50
|
作者
Ng, Sze-Sze [1 ]
Ho, Chun-Yu [1 ]
Schleicher, Kristin D. [1 ]
Jamison, Timothy F. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
nickel; alkenes; allenes; alkynes; aldehydes; isocyanates;
D O I
10.1351/pac200880050929
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several reactions of simple, unactivated alkenes with electrophiles under Ni(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes act as the functional equivalents of alkenyl- and allylmetal reagents.
引用
收藏
页码:929 / 939
页数:11
相关论文
共 50 条
  • [1] Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates
    Ng, Sze-Sze
    Ho, Chun-Yu
    Jamison, Timothy F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) : 11513 - 11528
  • [2] NICKEL-CATALYZED COUPLING OF ACTIVATED ALKENES WITH ORGANIC HALIDES
    BOLDRINI, GP
    SAVOIA, D
    TAGLIAVINI, E
    TROMBINI, C
    RONCHI, AU
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (03) : C62 - C64
  • [3] Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates
    Ng, Sze-Sze
    Ho, Chun-Yu
    Jamison, Timothy F.
    Journal of the American Chemical Society, 2006, 128 (35): : 11513 - 11528
  • [4] Photoinduced nickel-catalyzed enantioselective coupling reactions
    Li, Zhilong
    Li, Chengyang
    Ding, Yu
    Huo, Haohua
    COORDINATION CHEMISTRY REVIEWS, 2022, 460
  • [5] Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes
    Xiao, Jichao
    Montgomery, John
    ACS CATALYSIS, 2022, 12 (04) : 2463 - 2471
  • [6] Nickel-Catalyzed Dicarbofunctionalization of Alkenes
    Qi, Xiaoxu
    Diao, Tianning
    ACS CATALYSIS, 2020, 10 (15): : 8542 - 8556
  • [7] ELECTRON-TRANSFER IN NICKEL-CATALYZED COUPLING REACTIONS
    SCHWARTZ, J
    DAYRIT, FM
    LOOTS, MJ
    GLADKOWSKI, DE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 206 - INOR
  • [8] Nickel-catalyzed stereospecific cross-coupling reactions
    Jarvo, Elizabeth R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [9] Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions
    Diccianni, Justin B.
    Diao, Tianning
    TRENDS IN CHEMISTRY, 2019, 1 (09): : 830 - 844
  • [10] Preparation and nickel-catalyzed coupling reactions of divinylic selenides
    Silveira, CC
    Santos, PCS
    Braga, AL
    TETRAHEDRON LETTERS, 2002, 43 (42) : 7517 - 7520