Direct C-H Transformation via Iron Catalysis

被引:1867
作者
Sun, Chang-Liang
Li, Bi-Jie
Shi, Zhang-Jie [1 ]
机构
[1] Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China
关键词
CROSS-COUPLING REACTION; HECK-TYPE REACTION; STEREOSPECIFIC ALKANE HYDROXYLATION; OLEFIN CIS-DIHYDROXYLATION; ARYL BOND FORMATION; DIRECT ARYLATION; HYDROGEN-PEROXIDE; HIGHLY EFFICIENT; MIZOROKI-HECK; SELECTIVE OXIDATION;
D O I
10.1021/cr100198w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A compiled analysis and discussion of advances in iron-catalyzed C-H transformations in the past decade is presented. For the oxidation of cyclohexane, simpler and more efficient system were reported by using catalytic amounts of commercial available iron salts in acetonitrile under mild conditions, and H2O2 as the oxidant. In 2008, Fu and co-workers reported the first example of iron-catalyzed amidation of C-H bonds and a new C-N formation process was demonstrated by Li in 2010. In 2008, Nakamura and co-workers developed the first iron-catalyzed direct arylation of aryl C-H bonds with in situ generated organozinc reagents from aryl Grignard reagents and ZnCl2 in the presence of a proper ligand. Among direct C-H transformations, general alkyl sp3 C-H faces the highest challenge due to its intrinsic inactivating features.
引用
收藏
页码:1293 / 1314
页数:22
相关论文
共 321 条
  • [1] Reaction mechanisms of mononuclear non-heme iron oxygenases
    Abu-Omar, MM
    Loaiza, A
    Hontzeas, N
    [J]. CHEMICAL REVIEWS, 2005, 105 (06) : 2227 - 2252
  • [2] Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062
  • [3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [5] A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate
    Albone, DP
    Aujla, PS
    Taylor, PC
    Challenger, S
    Derrick, AM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9569 - 9571
  • [6] Amination of ethers using chloramine-T hydrate and a copper(I) catalyst
    Albone, DP
    Challenger, S
    Derrick, AM
    Fillery, SM
    Irwin, JL
    Parsons, CM
    Takada, H
    Taylor, PC
    Wilson, DJ
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 107 - 111
  • [7] Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
  • [8] 2-6
  • [9] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. TETRAHEDRON, 2005, 61 (50) : 11771 - 11835
  • [10] Synthesis of resveratrol using a direct decarbonylative Heck approach from resorcylic acid
    Andrus, MB
    Liu, J
    Meredith, EL
    Nartey, E
    [J]. TETRAHEDRON LETTERS, 2003, 44 (26) : 4819 - 4822