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

页码：571 / 579

页数：9

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