1,1-Carboboration of 1-Alkynes: A Conceptual Alternative to the Hydroboration Reaction

被引:104
作者
Chen, Chao [1 ]
Voss, Tanja [1 ]
Froehlich, Roland [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
CROSS-COUPLING REACTIONS; PI-COORDINATION; MONOHYDROBORATION REAGENT; ALKYNES; CHEMISTRY; CATIONS; BIS(PENTAFLUOROPHENYL)BORANE; 1,1-ORGANOBORATION; ACIDS; BOND;
D O I
10.1021/ol102544x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Strongly electrophilic boranes R-B(C6F5)(2) react readily with a variety of 1-alkynes by means of a 1,1-carboboration reaction to yield alkenylborane products, which can subsequently be used as reagents in metal catalyzed cross-coupling reactions.
引用
收藏
页码:62 / 65
页数:4
相关论文
共 38 条
[1]   Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media [J].
Alacid, Emilio ;
Najera, Carmen .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2321-2327
[2]  
[Anonymous], 1995, ANGEW CHEM
[3]   Solution structure, dynamics and speciation of perfluoroaryl boranes through 1H, 11B and 19F NMR spectroscopy [J].
Beringhelli, Tiziana ;
Donghi, Daniela ;
Maggioni, Daniela ;
D'Alfonso, Giuseppe .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (21-22) :2292-2313
[4]   REACTION OF ALKENYLBORONIC ACIDS WITH IODINE UNDER INFLUENCE OF BASE - SIMPLE PROCEDURE FOR STEREOSPECIFIC CONVERSION OF TERMINAL ALKYNES INTO TRANS-1-ALKENYL IODIDES VIA HYDROBORATION [J].
BROWN, HC ;
HAMAOKA, T ;
RAVINDRA.N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5786-5788
[5]   A NOVEL METHOD FOR SYNTHESIS OF BOTH CIS- AND TRANS-VINYL BROMIDES FROM 1-ALKYNES VIA HYDROBORATION [J].
BROWN, HC ;
BOWMAN, DH ;
MISUMI, S ;
UNNI, MK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4531-&
[7]  
CHA JS, 1993, TETRAHEDRON LETT, V34, P5113
[8]   Carbon-Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes [J].
Chen, Chao ;
Kehr, Gerald ;
Froehlich, Roland ;
Erker, Gerhard .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) :13594-13595
[9]   Exploring the Limits of Frustrated Lewis Pair Chemistry with Alkynes: Detection of a System that Favors 1,1-Carboboration over Cooperative 1,2-P/B-Addition [J].
Chen, Chao ;
Eweiner, Florian ;
Wibbeling, Birgit ;
Froehlich, Roland ;
Senda, Shunsuke ;
Ohki, Yasuhiro ;
Tatsumi, Kazuyuki ;
Grimme, Stefan ;
Kehr, Gerald ;
Erker, Gerhard .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (10) :2199-2208
[10]   TRANS-VINYLBORANES FROM 9-BORABICYCLO[3.3.1]NONANE THROUGH DEHYDROBORYLATION [J].
COLBERG, JC ;
RANE, A ;
VAQUER, J ;
SODERQUIST, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6065-6071