Push-pull alkenes bearing closo-decaborate cluster generated via nucleophilic addition of carbanions to borylated nitrilium salts

被引：14

作者：

Daines, Elena A. ^{[1
]}

Bolotin, Dmitrii S. ^{[1
]}

Bokach, Nadezhda A. ^{[1
]}

Gurzhiy, Vladislav V. ^{[2
]}

Zhdanov, Andrey P. ^{[3
]}

Zhizhin, Konstantin Yu. ^{[3
]}

Kuznetsov, Nikolay T. ^{[3
]}

机构：

[1] St Petersburg State Univ, Inst Chem, Univ Skaya Nab,7-9, St Petersburg 199034, Russia

[2] St Petersburg State Univ, Inst Earth Sci, Univ Skaya Nab 7-9, St Petersburg 199034, Russia

[3] Russian Acad Sci, NS Kurnakov Inst Gen & Inorgan Chem, Leninsky Pr,31, Moscow 119991, Russia

来源：

INORGANICA CHIMICA ACTA | 2018年 / 471卷

基金：

俄罗斯基础研究基金会;

关键词：

closo-Decaborate; Nucleophilic addition; Nitrile; Push-pull alkene; NEUTRON-CAPTURE THERAPY; 2-AMINO-1,1,3-TRICYANOPROPENE DIMERIC MALONONITRILE; B-H ACTIVATION; CONDENSATION PRODUCTS; CRYSTAL-STRUCTURES; ANION DERIVATIVES; 1ST EXAMPLE; BORON; COMPLEXES; METAL;

D O I：

10.1016/j.ica.2017.11.054

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Malonodinitrile, benzoylacetonitrile, and ethyl benzoylacetate were deprotonated in situ by (BuLi)-Bu-n to give the reactive carbanions (RRHC(-))-R-2-H-3 (R-2/R-3 = CN/CN, CN/COPh, CO2Et/COPh), which nucleophilically attack the C=N bond of the nitrilium clusters (Ph4P)[B10H9NCR1] (R-1 = Me, Et). This reaction results in generation of push-pull alkenes bearing closo-decaborate clusters, [B10H9NHC(R-1)=(CRR3)-R-2](2) (6 examples; up to 97% isolated yields). These species were isolated as the bis-tetraphenylposhphonium salts and were characterized by H-1 and B-11 NMR, HR ESI+/- -MS, and also by single-crystal X-ray diffraction. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：372 / 376

页数：5

共 61 条

[1] Cage Opening of a Carborane Ligand by Metal Cluster Complexes [J].

Adams, Richard D. ;

Kiprotich, Joseph ;

Peryshkov, Dmitry V. ;

Wong, Yuen Onn .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (19) :6501-6504

[2]

Allen F. K., 1987, J CHEM SOC P2, V12, pS1, DOI DOI 10.1039/P298700000S1

[3] 6-Amino-5-(1-amino-2,2-dicyanovinyl)-3,3a,4,5-tetrahydro-2H-indene-4-spiro-1′-cyclopentane-3a,7-dicarbonitrilethiophene-2-carbaldehyde(1/0.5) [J].

Asiri, Abdullah M. ;

Ng, Seik Weng .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 :O2484-U1700

[4] Blue Phosphorescent Zwitterionic Iridium(III) Complexes Featuring Weakly Coordinating nido-Carborane-Based Ligands [J].

Axtell, Jonathan C. ;

Kirlikovali, Kent O. ;

Djurovich, Peter I. ;

Jung, Dahee ;

Nguyen, Vinh T. ;

Munekiyo, Brian ;

Royappa, A. Timothy ;

Rheingold, Arnold L. ;

Spokoyny, Alexander M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (48) :15758-15765

[5] METAL-CATALYSIS VS BASE-CATALYSIS IN THE REACTIONS OF BETA-KETOAMIDES WITH CYANOGEN - SYNTHESIS OF MULTIFUNCTIONAL OLEFINS AND RELATED HETEROCYCLES [J].

BASATO, M ;

CAMPOSTRINI, R ;

CORAIN, B ;

DANGELI, F ;

VERONESE, AC ;

VALLE, G .

INORGANICA CHIMICA ACTA-ARTICLES AND LETTERS, 1985, 98 (02) :L17-L19

[6] Nucleophilic Addition of Aromatic Amide Oximes to [2-B10H9NCC2H5]- Anion [J].

Bolotin, D. S. ;

Demakova, M. Ya. ;

Daines, E. A. ;

Avdontseva, M. S. ;

Zhdanov, A. P. ;

Zhizhin, K. Yu. ;

Kuznetsov, N. T. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (01) :37-43

[7] Nucleophilicity of Oximes Based upon Addition to a Nitrilium closo-Decaborate Cluster [J].

Bolotin, Dmitrii S. ;

Burianova, Valeria K. ;

Novikov, Alexander S. ;

Demakova, Marina Ya. ;

Pretorius, Carla ;

Mokolokolo, Pennie Petrus ;

Roodt, Andreas ;

Bokach, Nadezhda A. ;

Suslonov, Vitaliy V. ;

Zhdanov, Andrey P. ;

Zhizhin, Konstantin Yu. ;

Kuznetsov, Nikolay T. ;

Kukushkin, Vadim Yu. .

ORGANOMETALLICS, 2016, 35 (20) :3612-3623

[8] Synthesis of the 1-hydroxy-closo-decaborate anion [1-B10H9OH]2- [J].

Bragin, VI ;

Sivaev, IB ;

Bregadze, VI ;

Votinova, NA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (11) :2847-2849

[9] The formulation of polyhedral boranes for the boron neutron capture therapy of cancer [J].

Calabrese, Gianpiero ;

Nesnas, John J. ;

Barbu, Eugen ;

Fatouros, Dimitris ;

Tsibouklis, John .

DRUG DISCOVERY TODAY, 2012, 17 (3-4) :153-159

[10] Iridium-catalysed regioselective borylation of carboranes via direct B-H activation [J].

Cheng, Ruofei ;

Qiu, Zaozao ;

Xie, Zuowei .

NATURE COMMUNICATIONS, 2017, 8

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