Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane

被引：70

作者：

Itami, K ^{[1
]}

Ushiogi, Y ^{[1
]}

Nokami, T ^{[1
]}

Ohashi, Y ^{[1
]}

Yoshida, JI ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synth Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol048620i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed the homocoupling reaction of alkenyl(2-pyridyl)silanes mediated by Cul and CsF, in which the strong directing effect of the 2-pyridyl group was observed. The homocoupling reaction was successfully integrated with the Mizoroki-Heck reaction of vinyl(2-pyridyl)silane with aryl halides, enabling a rapid and stereoselective synthesis of multisubstituted butadienes. From a relatively small compound library, it was possible to detect a number of fluorescent butadienes with a wide range of fluorescence color variations (blue to reddish-orange).

引用

页码：3695 / 3698

页数：4

共 19 条

[1] One-pot synthesis of oligomeric aryl-substituted PPV analogs with extended π-conjugation [J].

Feit, BA ;

Buzhansky, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (11) :1777-1782

[2] Diversity-oriented synthesis of multi substituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl) silane as a versatile platform for olefin synthesis [J].

Itami, K ;

Nokami, T ;

Ishimura, Y ;

Mitsudo, K ;

Kamei, T ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11577-11585

[3] Highly efficient carbopalladation across vinylsilane:: Dual role of the 2-PyMe2Si group as a directing group and as a phase tag [J].

Itami, K ;

Mitsudo, K ;

Kamei, T ;

Koike, T ;

Nokami, T ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12013-12014

[4] Palladium-catalyzed cross-coupling reaction of alkenyldimethyl(2-pyridyl)silanes with organic halides: Complete switch from the carbometalation pathway to the transmetalation pathway [J].

Itami, K ;

Nokami, T ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5600-5601

[5] Copper(I)-catalysed homocoupling of organosilicon compounds: Synthesis of biaryls, dienes and diynes [J].

Kang, SK ;

Kim, TH ;

Pyun, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :797-798

[6] SINGLE-LAYER WHITE LIGHT-EMITTING ORGANIC ELECTROLUMINESCENT DEVICES BASED ON DYE-DISPERSED POLY(N-VINYLCARBAZOLE) [J].

KIDO, J ;

SHIONOYA, H ;

NAGAI, K .

APPLIED PHYSICS LETTERS, 1995, 67 (16) :2281-2283

[7] Blue light emitting diode with 1,1,4,4-tetraphenyl-1,3-butadiene (TPB) [J].

Kim, JH ;

Noh, S ;

Kim, K ;

Lim, ST ;

Shin, DM .

SYNTHETIC METALS, 2001, 117 (1-3) :227-228

[8]

MUELLER R, 1970, J PRAKT CHEM, V312, P150

[9] Home-coupling reactions of alkenyl- and arylfluorosilanes mediated by a copper(I) salt [J].

Nishihara, Y ;

Ikegashira, K ;

Toriyama, F ;

Mori, A ;

Hiyama, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (04) :985-990

[10] TETRAPHENYLBUTADIENES VIA (1,1-DIPHENYLALLYL)LITHIUM [J].

SIMES, BE ;

RICKBORN, B ;

FLOURNOY, JM ;

BERLMAN, IB .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4613-4616

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