Synthesis of silafluorenes by iridium-catalyzed [2+2+2] cycloaddition of silicon-bridged diynes with alkynes

被引:117
作者
Matsuda, Takanori [1 ]
Kadowaki, Sho [1 ]
Goya, Tsuyoshi [1 ]
Murakami, Masahiro [1 ]
机构
[1] Kyoto Univ, Dept Synth Chem & Biol Chem, Katsura, Kyoto 6158510, Japan
关键词
D O I
10.1021/ol062732n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silicon-bridged 1,6-diynes underwent [2 + 2 + 2] cycloaddition with alkynes in the presence of an iridium(I)-phosphine catalyst to afford densely substituted silafluorene derivatives. Extended silafluorene skeletons were constructed by the [2 + 2 + 2] cycloaddition of tetraynes.
引用
收藏
页码:133 / 136
页数:4
相关论文
共 37 条
[1]   Poly(2,7-dibenzosilole): A blue light emitting polymer [J].
Chan, KL ;
McKiernan, MJ ;
Towns, CR ;
Holmes, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7662-7663
[2]   A general strategy for the facile synthesis of 2,7-dibromo-9-heterofluorenes [J].
Chen, RF ;
Fan, QL ;
Zheng, C ;
Huang, W .
ORGANIC LETTERS, 2006, 8 (02) :203-205
[3]   Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].
Gandon, Vincent ;
Aubert, Corinne ;
Malacria, Max .
CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217
[4]   A SILICON ANALOG OF 9,9-DIPHENYLFLUORENE [J].
GILMAN, H ;
GORSICH, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6380-6381
[5]   CYCLIC ORGANOSILICON COMPOUNDS .1. SYNTHESIS OF COMPOUNDS CONTAINING THE DIBENZOSILOLE NUCLEUS [J].
GILMAN, H ;
GORSICH, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (08) :1883-1886
[6]   Reactions of dilithiobutadienes with monochlorosilanes: Observation of facile loss of organic groups from silicon [J].
Hudrlik, PF ;
Dai, DH ;
Hudrlik, AM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) :1257-1264
[7]   CHEMISTRY OF SILOLES - THE REACTIONS OF SILOLES WITH ORGANO-LITHIUM REAGENTS [J].
ISHIKAWA, M ;
TABOHASHI, T ;
SUGISAWA, H ;
NISHIMURA, K ;
KUMADA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) :109-119
[8]   Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoynes and monoenes [J].
Kezuka, S ;
Tanaka, S ;
Ohe, T ;
Nakaya, Y ;
Takeuchi, R .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) :543-552
[9]  
Kulkarni AP, 2004, CHEM MATER, V16, P4556, DOI [10.1021/cm049473l, 10.1021/cm0494731]
[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