Synthesis of Benzo[b]siloles via KH-Promoted Cyclization of (2-Alkynylphenyl)silanes

被引：51

作者：

Ilies, Laurean ^{[1
]}

Tsuji, Hayato ^{[1
]}

Nakamura, Elichi ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 17期

关键词：

MEDIATED CYCLIZATION; ELECTRON-TRANSPORT; MODULAR SYNTHESIS; SILICON; DERIVATIVES; ALKYNES; BOND; BENZOSILOLES; REACTIVITY; DEVICES;

D O I：

10.1021/ol9015282

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2-Alkynylphenyl)silanes undergo intramolecular cyclization in the presence of an excess or a subequimolar amount of potassium hydride to give a variety of new 2-substituted benzosiloles in good to excellent yields. Some of these compounds showed a high fluorescence quantum yield both in solution and in the solid state, and they also showed reversible reduction in THF.

引用

页码：3966 / 3968

页数：3

共 30 条

[1] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[2]

CORRIU RJP, 1985, B SOC CHIM FR, P973

[3] ALKALI-METAL HYDRIDES - NEW METALLATING REAGENTS AT SILICON [J].

CORRIU, RJP ;

GUERIN, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (04) :168-169

[4] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724

[5] GROUP-14 METALLOLES .1. SYNTHESIS, ORGANIC-CHEMISTRY, AND PHYSICOCHEMICAL DATA [J].

DUBAC, J ;

LAPORTERIE, A ;

MANUEL, G .

CHEMICAL REVIEWS, 1990, 90 (01) :215-263

[6] THE STEREOCHEMISTRY OF NUCLEOPHILIC-SUBSTITUTION AT TETRACOORDINATED SILICON [J].

HOLMES, RR .

CHEMICAL REVIEWS, 1990, 90 (01) :17-31

[7] Modular synthesis of functionalized benzosiloles by tin-mediated cyclization of (o-alkynylphenyl)silane [J].

Ilies, Laurean ;

Tsuji, Hayato ;

Sato, Yoshiharu ;

Nakamura, Eiichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) :4240-+

[8]

Kulkarni AP, 2004, CHEM MATER, V16, P4556, DOI [10.1021/cm049473l, 10.1021/cm0494731]

[9] SILICON-CARBON UNSATURATED-COMPOUNDS .46. NICKEL-CATALYZED REACTION OF 2-TOLYLHEXAMETHYLTRISILANES AND 2-PHENYL-2-(PHENYLETHYNYL) HEXAMETHYLTRISILANES IN THE PRESENCE OF 2,3-DIMETHYLBUTADIENE AND DICYCLOPENTADIENE [J].

KUNAI, A ;

YUZURIHA, Y ;

NAKA, A ;

ISHIKAWA, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) :77-81

[10] Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives [J].

Lee, SH ;

Jang, BB ;

Kafafi, ZH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9071-9078

← 1 2 3 →