Olefin-Borane "van der Waals Complexes": Intermediates in Frustrated Lewis Pair Addition Reactions

被引：94
|
作者：
Zhao, Xiaoxi [1 ]
Stephan, Douglas W. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 32期
基金：
加拿大自然科学与工程研究理事会;
关键词：
FREE CATALYTIC-HYDROGENATION; SPECTROSCOPIC CHARACTERIZATION; DENSITY FUNCTIONALS; DYNAMIC PROPERTIES; METAL; MODELS; REACTIVITY; CHEMISTRY; MECHANISM; KINETICS;
D O I：
10.1021/ja205598k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The nature of the borane-olefin interactions that take place prior to frustrated Lewis pair addition reactions has been probed employing a Lewis acidic borane tethered to a vinyl group through an alkyl chain. H-1{F-19} HOESY spectral data obtained at -50 degrees C demonstrated the spatial proximity of the boryl and vinyl groups and computational data support the initial formation of a van der Waals borane-olefin complex. Such species serve as intermediates undergoing facile addition reactions with phosphine bases to afford cyclic zwitterionic products.
引用
收藏
页码：12448 / 12450
页数：3
相关论文
共 41 条
  • [31] Reactions of oxygen atoms with van der Waals complexes: The effect of complex formation on the internal energy distribution in the products
    McCoy, AB
    Lufaso, MW
    Veneziani, M
    Atrill, S
    Naaman, R
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (23): : 9651 - 9657
  • [32] Transition state observation of excited harpoon reactions, within Ca-HX van der Waals complexes
    Keller, A
    Lawruszczuk, R
    Soep, B
    Visticot, JP
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1996, 105 (11): : 4556 - 4564
  • [33] COUPLED-PAIR FUNCTIONAL CALCULATIONS ON THE AR-CO AND AR2 VAN-DER-WAALS COMPLEXES
    JANSEN, G
    [J]. CHEMICAL PHYSICS LETTERS, 1994, 223 (04) : 377 - 382
  • [34] Lone pair interactions with coinage metal atoms: Weak van der Waals complexes of the coinage metal atoms with water and ammonia
    Antusek, A
    Urban, M
    Sadlej, AJ
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2003, 119 (14): : 7247 - 7262
  • [35] Reversed Lewis acidity of mixed boron halides: An infrared study of the van der Waals complexes of BFxCly with CH3F in cryosolution
    vanderVeken, BJ
    Sluyts, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (47) : 11516 - 11522
  • [36] Reaction of Diphenylphosphanylacetylene with RB(C6F5)2 Reagents: Evidence for a Remarkable Sequence of Synergistic Frustrated Lewis Pair Addition Reactions
    Yu, Jiangang
    Kehr, Gerald
    Daniliuc, Constantin G.
    Erker, Gerhard
    [J]. INORGANIC CHEMISTRY, 2013, 52 (19) : 11661 - 11668
  • [37] Addition reactions to the intramolecular mesityl2P-CH2-CH2-B(C6F5)2 frustrated Lewis pair
    Moemming, Cornelia M.
    Kehr, Gerald
    Wibbeling, Birgit
    Froehlich, Roland
    Erker, Gerhard
    [J]. DALTON TRANSACTIONS, 2010, 39 (32) : 7556 - 7564
  • [38] Effective utilization of noncovalent interaction descriptor in BX3-Lewis base complexes: A determination of adduct/van der Waals complexes and reassessment of the BX3 acid strength order
    Lu, Renqing
    Zhao, Yuxin
    Lin, Jin
    Zhao, Xin
    [J]. CHEMICAL PHYSICS LETTERS, 2015, 636 : 117 - 120
  • [39] Scandium complexes containing β-diketiminato ligands with pendant phosphanyl groups: competition between Sc/γ-C [4+2] cycloaddition and Sc/P frustrated Lewis pair reactions
    Yao, Tu
    Xu, Pengfei
    Xu, Xin
    [J]. DALTON TRANSACTIONS, 2019, 48 (22) : 7743 - 7754
  • [40] Inclusion of ion-pair states in the diatomics-in-molecules description of potential energy surfaces: van der Waals complexes of He-Cl-2 and Ar-Cl-2
    Grigorenko, BL
    Nemukhin, AV
    Apkarian, VA
    [J]. CHEMICAL PHYSICS, 1997, 219 (2-3) : 161 - 172
12345