Copper-catalyzed cross-coupling of 1-haloalkyl-o-carboranes with Grignard reagents: an efficient route to monosubstituted o-carborane derivatives

被引：11

作者：

Lu, Ju-You ^{[1
]}

Du, Yongmei ^{[1
]}

Zhao, Bo ^{[1
]}

Lu, Jian ^{[1
]}

机构：

[1] Xian Modern Chem Res Inst, Xian 710065, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Copper-catalyzed; Cross-coupling; Carborane; Grignard reagent; Synthetic method; ALKYL-HALIDES; STRUCTURAL-CHARACTERIZATION; DELIVERY VEHICLES; CANCER-THERAPY; CHEMISTRY; DECABORANE; INSERTION; METALLACARBORANES; HYDROBORATION; CLOSOMERS;

D O I：

10.1016/j.tet.2015.11.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and efficient copper-catalyzed reaction has been developed for the synthesis of functionalized o-carborane derivatives by using a Cu/phosphine catalytic system. Cross-coupling of readily available 1-haloalkyl-o-carboranes with Grignard reagents proceeds efficiently under mild conditions, and the corresponding monosubstituted o-carboranes were obtained in good to excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：161 / 169

页数：9

共 55 条

[1] Synthesis of an o-carboranyl derivative of 4-[5-(4-methyl-1-piperazinyl)-2,5′-bi-1H-benzimidazol-2′-yl]phenol [J].

Argentini, M ;

Dos Santos, DF ;

Weinreich, R ;

Hansen, HJ .

INORGANIC CHEMISTRY, 1998, 37 (23) :6018-6022

[2] Synthesis of unsymmetrical N-carboranyl NHCs: directing effect of the carborane anion [J].

Asay, Matthew J. ;

Fisher, Steven P. ;

Lee, Sarah E. ;

Tham, Fook S. ;

Borchardt, Dan ;

Lavallo, Vincent .

CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5359-5362

[3] Acid-Induced Opening of [closo-B10H10]2- as a New Route to 6-Substituted nido-B10H13 Decaboranes and Related Carboranes [J].

Bondarev, Oleg ;

Sevryugina, Yulia V. ;

Jalisatgi, Satish S. ;

Hawthorne, M. Frederick .

INORGANIC CHEMISTRY, 2012, 51 (18) :9935-9942

[4] DICARBA-CLOSO-DODECABORANES C2B10H12 AND THEIR DERIVATIVES [J].

BREGADZE, VI .

CHEMICAL REVIEWS, 1992, 92 (02) :209-223

[5] Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].

Cárdenas, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387

[6] Synthesis and structural characterization of hydroxyethyl- and alkoxyethyl-o-carboranes and their alkali and rare earth metal complexes [J].

Cheung, MS ;

Chan, HS ;

Xie, ZW .

ORGANOMETALLICS, 2004, 23 (03) :517-526

[7] Synthesis and Properties of Carborane-Appended C3-Symmetrical Extended π Systems [J].

Dash, Barada Prasanna ;

Satapathy, Rashmirekha ;

Gaillard, Elizabeth R. ;

Maguire, John A. ;

Hosmane, Narayan S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (18) :6578-6587

[8] Deboronation of ortho-carborane by an iminophosphorane:: crystal structures of the novel carborane adduct nido-C2B10H12•HNP(NMe2)3 and the borenium salt [(Me2N)3PNHBNP(NMe2)3]2O2+(C2B9H12-)2 [J].

Davidson, MG ;

Fox, MA ;

Hibbert, TG ;

Howard, JAK ;

Mackinnon, A ;

Neretin, IS ;

Wade, K .

CHEMICAL COMMUNICATIONS, 1999, (17) :1649-1650

[9]

El- Zaria M. E., 2014, ANGEW CHEM, V126, P5256

[10] CARBORANES .1. PREPARATION AND CHEMISTRY OF 1-ISOPROPENYLCARBORANE AND ITS DERIVATIVES (A NEW FAMILY OF STABLE CLOVOBORANES) [J].

FEIN, MM ;

COHEN, MS ;

MAYES, N ;

SCHWARTZ, N ;

BOBINSKI, J .

INORGANIC CHEMISTRY, 1963, 2 (06) :1111-&

← 1 2 3 4 5 6 →