Insertion Reactions of Diazomethanes and Electrophilic Boranes

被引:25
作者
Neu, Rebecca C. [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
SITE OLEFIN POLYMERIZATION; BIFUNCTIONAL PERFLUOROARYL BORANES; FRUSTRATED LEWIS PAIRS; ORGANOBORON POLYMERS; BINUCLEAR CATALYSTS; ACID CATALYSTS; BORON; REACTIVITY; CHEMISTRY; 1,1-CARBOBORATION;
D O I
10.1021/om2011613
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The electrophilic pentafluoroarylboranes B-(C6F5)(3), PhB(C6F5)(2), and ClB(C6F5)(2) react with (trimethylsilyl) diazomethane, diphenyldiazomethane, or (pentafluorophenyl)diazomethane, affording insertion into the one or two B-C bonds in a facile and high-yielding route to the boranes (Me3SiCH(C6F5))B(C6F5)(2), (Me3SiCH-(C6F5))(2)B(C6F5), (Me3SiCH(C6F5))(Me3SiCH(Ph))B-(C6F5), (C6F5)ClB(CPh2(C6F5)), and (C6F5)(2)B(CH(C6F5)(2)).
引用
收藏
页码:46 / 49
页数:4
相关论文
共 81 条
[1]   Reaction of boranes with TMS diazomethane and dimethylsulfoxonium methylide.: Synthesis of poly(methylidene-co-TMSmethylidene) random copolymers [J].
Bai, Jie ;
Shea, Kenneth J. .
MACROMOLECULAR RAPID COMMUNICATIONS, 2006, 27 (15) :1223-1228
[2]  
Bochmann M., 2003, BOR CHEM BEG 21 CENT, P285
[3]   Polyfluorenes with on-chain dibenzoborole units -: Synthesis and anion-induced photoluminescence quenching [J].
Bonifacio, Vasco D. B. ;
Morgado, Jorge ;
Scherf, Ullrich .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (08) :2878-2883
[4]   From B(C6F5)3 to B(OC6F5)3:: Synthesis of (C6F5)2BOC6F5 and C6F5B(OC6F5)2 and their relative lewis acidity [J].
Britovsek, GJP ;
Ugolotti, J ;
White, AJP .
ORGANOMETALLICS, 2005, 24 (07) :1685-1691
[5]   New Synthetic Strategies for Structured Silicones Using B(C6F5)3 [J].
Brook, Michael A. ;
Grande, John B. ;
Ganachaud, Francois .
SILICON POLYMERS, 2011, 235 :161-183
[6]   Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes [J].
Burgos, CH ;
Canales, E ;
Matos, K ;
Soderquist, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8044-8049
[7]   Synthesis of Functionalizable Boron-Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings [J].
Caruso, Anthony, Jr. ;
Siegler, Maxime A. ;
Tovar, John D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) :4213-4217
[8]   Organoboron Polymers for Photovoltaic Bulk Heterojunctions [J].
Cataldo, Sebastiano ;
Fabiano, Simone ;
Ferrante, Francesco ;
Previti, Francesco ;
Patane, Salvatore ;
Pignataro, Bruno .
MACROMOLECULAR RAPID COMMUNICATIONS, 2010, 31 (14) :1281-1286
[9]   Synthesis and electrochemical properties of a new class of boron-containing n-type conjugated polymers [J].
Chai, Jianfang ;
Wang, Chao ;
Jia, Li ;
Pang, Yi ;
Graham, Matthew ;
Cheng, Stephen Z. D. .
SYNTHETIC METALS, 2009, 159 (14) :1443-1449
[10]   Metal-free catalytic hydrogenation (vol 46, pg 8050, 2007) [J].
Chase, P. A. ;
Welch, G. C. ;
Jurca, T. ;
Stephan, D. W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9136-9136