Carbon-halogen bond activation by a structurally constrained phosphorus(Ⅲ)platform

被引:1
|
作者
Penglong Wang [1 ]
Qin Zhu [1 ,2 ,3 ]
Yi Wang [1 ]
Guixiang Zeng [2 ]
Jun Zhu [3 ]
Congqing Zhu [1 ]
机构
[1] State Key Laboratory of Coordination Chemistry,Jiangsu Key Laboratory of Advanced Organic Materials,School of Chemistry and Chemical Engineering,Nanjing University
[2] Kuang Yaming Honors School,Institute for Brain Sciences,Nanjing University
[3] State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials(iChEM),and Department of Chemistry,College of Chemistry and Chemical Engineering,Xiamen University
基金
中国国家自然科学基金;
关键词
D O I
暂无
中图分类号
O621.25 [];
学科分类号
070303 ; 081704 ;
摘要
The σ-bond activation by main group element has received enormous attention from theoretical and experimental chemists.Here,the reaction of C-X(X=Cl,Br,I) bonds in benzyl and allyl halides with a pincer-type phosphorus(Ⅲ) species was reported.A series of structurally robust phosphorus(Ⅴ)compounds were formed via the formal oxidative addition reactions of C-X bonds to the phosphorus(Ⅲ)center.Density functional theory calculations show that the nucleophilic addition process is more favorable than the direct oxidative addition mechanism.Isomerization of bent structures of phosphorus(Ⅲ) compound to poorly nucleophilic compounds to undergo further C-X bond activation can be rationalized by frontier molecule orbital analysis.This study not only provides a deep understanding of the reactivity of phosphorus(Ⅲ) species but also demonstrates a potential of main group elements for the small-molecule activation.
引用
收藏
页码:1432 / 1436
页数:5
相关论文
共 50 条
  • [1] Carbon-halogen bond activation by a structurally constrained phosphorus(III) platform
    Wang, Penglong
    Zhu, Qin
    Wang, Yi
    Zeng, Guixiang
    Zhu, Jun
    Zhu, Congqing
    [J]. CHINESE CHEMICAL LETTERS, 2021, 32 (04) : 1432 - 1436
  • [2] Carbon-halogen bond activation by halogen bond donors
    Huber, Stefan M.
    Walter, Sebastian M.
    Kniep, Florian
    Herdtweck, Eberhard
    Rout, Laxmidhar
    Bensch, Heide K. V.
    Jungbauer, Stefan H.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [3] Phosphorus Analogues of [Ni(bpy)2]: Synthesis and Application in Carbon-Halogen Bond Activation
    Leitl, J.
    Coburger, P.
    Scott, D. J.
    Ziegler, C. G. P.
    Hierlmeier, G.
    Wolf, R.
    van Leest, N. P.
    de Bruin, B.
    Hoerner, G.
    Mueller, C.
    [J]. INORGANIC CHEMISTRY, 2020, 59 (14) : 9951 - 9961
  • [4] CARBON-HALOGEN BOND ENERGIES AND BOND DISTANCES
    GLOCKLER, G
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1959, 63 (06): : 828 - 832
  • [5] REACTION OF DIPHENYLMETHYLENE WITH CARBON-HALOGEN BOND
    MURRAY, RW
    TROZZOLO, AM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (09): : 3341 - &
  • [6] The Raman effect and the carbon-halogen bond
    Harkins, WD
    Bowers, HE
    [J]. PHYSICAL REVIEW, 1931, 38 (10): : 1845 - 1857
  • [7] Catalytic carbon-halogen bond activation: Trends in reactivity, selectivity, and solvation
    de Jong, G. Theodoor
    Bickelhaupt, F. Matthias
    [J]. JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2007, 3 (02) : 514 - 529
  • [8] CARBON-HALOGEN BOND ACTIVATION AT RU3(CO)12
    AIME, S
    OSELLA, D
    DEEMING, AJ
    LANFREDI, AMM
    TIRIPICCHIO, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 244 (03) : C47 - C49
  • [9] Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding
    Wonner, Patrick
    Vogel, Lukas
    Dueser, Maximilian
    Gomes, Luis
    Kniep, Florian
    Mallick, Bert
    Werz, Daniel B.
    Huber, Stefan M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) : 12009 - 12012
  • [10] Bond activation by iminophosphoranes with geometrically constrained phosphorus platform
    Lin, Yi-Chun
    Radosevich, Alexander
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248