Developing carbon Lewis base/boron Lewis acid frustrated Lewis pair chemistry derived from conjugated dienamines

被引：5
|
作者：
Moericke, Jennifer [1 ]
Rehwinkel, Florian [1 ]
Danelzik, Tobias [1 ]
Daniliuc, Constantin G. [1 ]
Wibbeling, Birgit [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构：
[1] Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany
来源：
TETRAHEDRON | 2019年 / 75卷 / 05期
关键词：
Frustrated Lewis pairs; Main group element chemistry; Boron; HETEROLYTIC DIHYDROGEN ACTIVATION; N-HETEROCYCLIC CARBENE; N-HETEROCYCLE-B(C6F5)(3) COMPLEXES; C-H; REACTIVITY; HYDROGEN; GENERATION; B(C6F5)(3); 1,4-HYDROBORATION; BIS(PENTAFLUOROPHENYL)BORANE;
D O I：
10.1016/j.tet.2018.11.068
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several dienamines R2N-CH=CH-CH=CMe2 react with Piers' borane by HB(C6F5)(2) addition to the terminal -CH=CMe2 unit to form the isopropyl substituted products 14. The strongly electrophilic -B(C6F5)(2) functionality at the C3 position of the chain shows a marked contact to the adjacent enamine beta-carbon atom C2. This generates a pronounced C/B FLP character which chemically comes to bear in the 1,2 addition reactions to the C=O bond of benzaldehyde or the -C N bonds of a series of alkylcyanides. In some cases, the formation of uncommon rearrangement products is observed. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：571 / 579
页数：9
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