Borane-Induced Dimerization of Arylallenes

被引:16
作者
Tao, Xin [1 ]
Daniliuc, Constantin G. [1 ]
Dittrich, Dustin [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
allenes; boron; dimerization; rearrangements; reaction mechanisms; FREE HYDROGEN ACTIVATION; FRUSTRATED LEWIS PAIRS; COPE REARRANGEMENT; ORGANOBORON COMPOUNDS; ASYMMETRIC-SYNTHESIS; ALLENES; HYDROBORATION; CHEMISTRY; OLEFINS; COMPLEXES;
D O I
10.1002/anie.201808436
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of arylallenes react with HB(C6F5)(2) in a 2:1 molar ratio to give the tail-to-tail 1,6-diaryl-2-boryl-hexa-1,5-diene coupling products. The reaction of the phenylallene substrate with HB(C6F5)(2) was shown to initially give the 2-boryl-3,4-diphenyl-1,5-hexadiene head-to-head coupling product which then rearranged, by a thermally induced Cope rearrangement, into the final product.
引用
收藏
页码:13922 / 13926
页数:5
相关论文
共 77 条
[1]   Progress in allene chemistry [J].
Alcaide, Benito ;
Almendros, Pedro .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :2886-2887
[2]  
[Anonymous], 1995, Angew. Chem, V107, P895
[3]  
[Anonymous], 2010, ANGEW CHEM, V122, P50
[4]  
[Anonymous], 2000, ANGEW CHEM, V112, P3737
[5]  
[Anonymous], 2012, ANGEW CHEM, V124, P3128
[6]  
[Anonymous], 2007, ANGEW CHEM, V119, P5056
[7]  
[Anonymous], 2015, ANGEW CHEM, V127, P6498
[9]   HYDROBORATION OF OLEFINS - A REMARKABLY FAST ROOM-TEMPERATURE ADDITION OF DIBORANE TO OLEFINS [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (09) :1136-1137
[10]   HYDROBORATION .51. HYDROBORATION OF REPRESENTATIVE ALLENES WITH 9-BORABICYCLO[3.3.1]NONANE - EXCEPTIONAL DIRECTIVE EFFECT PROVIDING A DIRECT SYNTHESIS OF B-ALLYL-9-BORABICYCLO[3.3.1]NONANE DERIVATIVES [J].
BROWN, HC ;
LIOTTA, R ;
KRAMER, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (11) :2966-2970