Rhodium-catalyzed anti selective cross-addition of bis(trimethylsilyl)-acetylene to diarylacetylenes via carbon-silicon bond cleavage

被引：16

作者：

Horita, Akinobu ^{[1
]}

Tsurugi, Hayato ^{[1
]}

Satoh, Tetsuya ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 09期

关键词：

D O I：

10.1021/ol8004003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of bis(trimethylsilyl)acetylene to diarylacetylenes proceeds efficiently and selectively in a formal anti fashion in the presence of [Rh(OH)(cod)](2)/bisphosphine and phenol as catalyst and activator, respectively, accompanied by cleavage of one of the C-Si bonds to produce the corresponding (Z)-enynes. The products can further couple with the same or a different diarylacetylene molecule to give rise to (ZZ)-1,2,5,6-tetraaryl-1,5-hexadien-3-ynes that show relatively strong solid-state fluorescence.

引用

页码：1751 / 1754

页数：4

共 30 条

[1] REGIOSELECTIVE HOMOMERIZATION AND CODIMERIZATION OF 1-ALKYNES LEADING TO 2,4-DISUBSTITUTED 1-BUTEN-3-YNES BY CATALYSIS OF A (ETA-5-C5ME5)2TICL2/RMGX SYSTEM [J].

AKITA, M ;

YASUDA, H ;

NAKAMURA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (02) :480-487

[2] Facile and selective copper-palladium catalyzed addition of terminal alkynes to activated alkynes in water [J].

Chen, L ;

Li, CJ .

TETRAHEDRON LETTERS, 2004, 45 (13) :2771-2774

[3]

FANGOU K, 2003, CHEM REV, V103, P169

[4] Regio- and stereoselective homocoupling of γ-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives [J].

Funayama, A ;

Satoh, T ;

Miura, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15354-15355

[5] Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].

Hayashi, T ;

Inoue, K ;

Taniguchi, N ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919

[6] Iridium complex-catalyzed cross-coupling reaction of terminal alkynes with internal alkynes via C-H activation of terminal alkynes [J].

Hirabayashi, T ;

Sakaguchi, S ;

Ishii, Y .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (06) :872-876

[7]

Hiyama T, 2002, TOP CURR CHEM, V219, P61

[8] Regio- and stereoselective cross-coupling of tert-propargyl alchols with bis(trimethylsilyl)acetylene and its utilization in constructing a fluorescent donor-acceptor system [J].

Horita, Akinobu ;

Tsurugi, Hayato ;

Funayama, Atsushi ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2007, 9 (11) :2231-2233

[9] SYNTHESIS AND PROPERTIES OF 1,2,5,6-TETRAPHENYLHEXA-1,5-DIENE-3-YNE [J].

ISRAELASHVILI, S ;

EDLITZPFEFFERMANN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (22) :5780-5782

[10] Cross-coupling of alkynes catalyzed by Phebox-rhodium acetate complexes [J].

Ito, Jun-ichi ;

Kitase, Megumi ;

Nishiyama, Hisao .

ORGANOMETALLICS, 2007, 26 (25) :6412-6417

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