Frustrated Lewis pairs: reactivities of TMS protected amines and phosphines in the presence of B(C6F5)3

被引:33
作者
Schulz, Felix [1 ]
Sumerin, Victor [2 ]
Leskela, Markku [2 ]
Repo, Timo [2 ]
Rieger, Bernhard [1 ]
机构
[1] Tech Univ Munich, WACKER Lehrstuhl Makromol Chem, D-85747 Garching, Germany
[2] Univ Helsinki, Inorgan Chem Lab, Dept Chem, FIN-00014 Helsinki, Finland
关键词
FREE CATALYTIC-HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; METAL-FREE; BULKY PROTON; IMINES; MECHANISM; SELECTIVITY; REDUCTION; COMPLEXES; CLEAVAGE;
D O I
10.1039/b923196j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
TMS protected amines in combination with B(C6F5)(3) were found to activate H2 and this is followed by a cleavage of the N-Si bond and the generation of TMSH. A TMS protected phosphine on the other hand reacts rapidly with B(C6F5)(3) to give the known compound tBu(2)P(C6F4)B(C6F5)(2) by a facile and efficient route.
引用
收藏
页码:1920 / 1922
页数:3
相关论文
共 62 条
[1]   Catalytic Hydrogenation of Sensitive Organometallic Compounds by Antagonistic N/B Lewis Pair Catalyst Systems [J].
Axenov, Kirill V. ;
Kehr, Gerald ;
Froehlich, Roland ;
Erker, Gerhard .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) :3454-+
[2]   Quantum-chemical study on positional selectivity in the trimethylsilylation and sulfonation of pyrrole and N-alkylpyrroles [J].
Belen'kii, L. I. ;
Chuvylkin, N. D. ;
Serykh, A. I. ;
Suslov, I. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (09) :1337-1340
[3]   B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers [J].
Blackwell, JM ;
Morrison, DJ ;
Piers, WE .
TETRAHEDRON, 2002, 58 (41) :8247-8254
[4]   Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes:: Is hypercoordination at boron responsible? [J].
Blackwell, JM ;
Piers, WE ;
Parvez, M .
ORGANIC LETTERS, 2000, 2 (05) :695-698
[5]   B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates [J].
Blackwell, JM ;
Sonmor, ER ;
Scoccitti, T ;
Piers, WE .
ORGANIC LETTERS, 2000, 2 (24) :3921-3923
[6]   B(C6F5)3-catalyzed silation of alcohols:: A mild, general method for synthesis of silyl ethers [J].
Blackwell, JM ;
Foster, KL ;
Beck, VH ;
Piers, WE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4887-4892
[7]   Fluorinated 9-borafluorenes vs. conventional perfluoroaryl boranes - Comparative Lewis acidity [J].
Chase, PA ;
Romero, PE ;
Piers, WE ;
Parvez, M ;
Patrick, BO .
CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (12) :2098-2105
[8]   Hydrogen and amine activation by a frustrated Lewis pair of a bulky n-heterocyclic carbene and B(C6F5)3 [J].
Chase, Preston A. ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7433-7437
[9]   Lewis acid-catalyzed hydrogenation:: B(C6F5)3-mediated reduction of imines and nitriles with H2 [J].
Chase, Preston A. ;
Jurca, Titel ;
Stephan, Douglas W. .
CHEMICAL COMMUNICATIONS, 2008, (14) :1701-1703
[10]   Metal-free catalytic hydrogenation [J].
Chase, Preston A. ;
Welch, Gregory C. ;
Jurca, Titel ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053