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

被引:38
作者
Horita, Akinobu [1 ]
Tsurugi, Hayato [1 ]
Funayama, Atsushi [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ol070799k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp(3)) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives.
引用
收藏
页码:2231 / 2233
页数:3
相关论文
共 36 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]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313
[3]   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
[4]  
FANGOU K, 2003, CHEM REV, V103, P169
[5]   CHEMISTRY OF LACTONES .5. REACTION OF ALPHA-BENZYLIDENE-GAMMA-PHENYL-DELTA BETA,GAMMA-BUTENOLIDE WITH PHENYLMAGNESIUM BROMIDE AND PHENYLLITHIUM [J].
FILLER, R ;
PIASEK, EJ ;
MARK, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (08) :2659-&
[6]   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
[7]   Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures [J].
Grabowski, ZR ;
Rotkiewicz, K ;
Rettig, W .
CHEMICAL REVIEWS, 2003, 103 (10) :3899-4031
[8]   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
[9]  
Jun CH, 2002, CHEM-EUR J, V8, P2423, DOI 10.1002/1521-3765(20020603)8:11<2422::AID-CHEM2422>3.0.CO
[10]  
2-B