Mechanisms of Bisphosphine Iron-Catalyzed C(SP2)-C(SP3) Cross-Coupling Reactions: Inner-Sphere or Outer-Sphere Arylation?

被引：7
作者：
Liu, Lei [1 ]
Lee, Wes [1 ]
Yuan, Mingbin [1 ]
Gutierrez, Osvaldo [1 ]
机构：
[1] Univ Maryland, Dept Chem & Biochem, 0107 Chem Bldg,8051 Regents Dr, College Pk, MD 20742 USA
来源：
COMMENTS ON INORGANIC CHEMISTRY | 2018年 / 38卷 / 06期
基金：
美国国家科学基金会;
关键词：
Iron; Catalysis; Density Functional Theory; DENSITY-FUNCTIONAL THEORY; MAGNETIC CIRCULAR-DICHROISM; MOLECULAR-ORBITAL METHODS; 2ND-ORDER PERTURBATION-THEORY; ARYL-GRIGNARD-REAGENTS; GAUSSIAN-BASIS SETS; ELECTRONIC-STRUCTURE; SPIN-STATE; ALKYL-HALIDES; GROUND-STATE;
D O I：
10.1080/02603594.2018.1539392
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
In this comment, we present recent insights into the mechanism of bisphosphine-iron catalyzed C(sp(2))-C(sp(3)) cross-coupling reactions (CCRs) with the focus on the nature of the C-C bond formation event (inner-sphere versus outer-sphere) as revealed by quantum mechanical calculations from our group and others. Implications for reaction and catalyst design principles are discussed.
引用
收藏
页码：210 / 237
页数：28
相关论文
共 158 条
  • [1] Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals
    Adak, Laksmikanta
    Kawamura, Shintaro
    Toma, Gabriel
    Takenaka, Toshio
    Isozaki, Katsuhiro
    Takaya, Hikaru
    Orita, Akihiro
    Li, Ho C.
    Shing, Tony K. M.
    Nakamura, Masaharu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) : 10693 - 10701
  • [2] Iron(I) in Negishi Cross-Coupling Reactions
    Adams, Christopher J.
    Bedford, Robin B.
    Carter, Emma
    Gower, Nicholas J.
    Haddow, Mairi F.
    Harvey, Jeremy N.
    Huwe, Michael
    Angeles Cartes, M.
    Mansell, Stephen M.
    Mendoza, Carla
    Murphy, Damien M.
    Neeve, Emily C.
    Nunn, Joshua
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10333 - 10336
  • [3] Isolation and Characterization of a Tetramethyliron(III) Ferrate: An Intermediate in the Reduction Pathway of Ferric Salts with MeMgBr
    Al-Afyouni, Malik H.
    Fillman, Kathlyn L.
    Brennessel, William W.
    Neidig, Michael L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) : 15457 - 15460
  • [4] The performance of density functional based methods in the description of selected biological systems and processes
    Alberto, Marta E.
    Marino, Tiziana
    Russo, Nino
    Sicilia, Emilia
    Toscano, Marirosa
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2012, 14 (43) : 14943 - 14953
  • [5] 2ND-ORDER PERTURBATION-THEORY WITH A COMPLETE ACTIVE SPACE SELF-CONSISTENT FIELD REFERENCE FUNCTION
    ANDERSSON, K
    MALMQVIST, PA
    ROOS, BO
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1992, 96 (02) : 1218 - 1226
  • [6] DIFFERENT FORMS OF THE 0TH-ORDER HAMILTONIAN IN 2ND-ORDER PERTURBATION-THEORY WITH A COMPLETE ACTIVE SPACE SELF-CONSISTENT-FIELD REFERENCE FUNCTION
    ANDERSSON, K
    [J]. THEORETICA CHIMICA ACTA, 1995, 91 (1-2): : 31 - 46
  • [7] 2ND-ORDER PERTURBATION-THEORY WITH A CASSCF REFERENCE FUNCTION
    ANDERSSON, K
    MALMQVIST, PA
    ROOS, BO
    SADLEJ, AJ
    WOLINSKI, K
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) : 5483 - 5488
  • [8] INCORPORATION OF SOLVENT EFFECTS INTO DENSITY-FUNCTIONAL CALCULATIONS OF MOLECULAR-ENERGIES AND GEOMETRIES
    ANDZELM, J
    KOLMEL, C
    KLAMT, A
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1995, 103 (21) : 9312 - 9320
  • [9] [Anonymous], J CHEM PHYS
  • [10] [Anonymous], 2015, US DEP HLTH HUMAN SE
12345678910