Synthesis of functionalized carbon-sulfur [5]Helicene:: Pd-catalyzed Negishi cross-coupling between the β-positions of thiophenes

被引:43
作者
Miyasaka, M [1 ]
Rajca, A [1 ]
机构
[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
关键词
helical structures; cross-coupling; alkylthiophene; helicene; oligothiophene;
D O I
10.1055/s-2003-43335
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Octyl- and bromo-substituted carbon-sulfur [5]helicene was prepared in several steps starting from either thiophene or 3-bromothiophene. Pd-catalyzed Negishi cross-coupling between the beta-positions of thiophenes was one of the key steps in the synthesis.
引用
收藏
页码:177 / 181
页数:5
相关论文
共 50 条
[1]  
BRANDSMA L, 1994, RECL TRAV CHIM PAY B, V113, P529
[2]   C4S8;2- and C16S18;4-:: Intermediates in the synthesis of poly(carbonsulfide) [J].
Chou, JH ;
Rauchfuss, TB .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1997, 52 (12) :1549-1552
[3]   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
[4]   Selective electrochemical mono- and polysilylation of halothiophenes [J].
Deffieux, D ;
Bonafoux, D ;
Bordeau, M ;
Biran, C ;
Dunogues, J .
ORGANOMETALLICS, 1996, 15 (08) :2041-2046
[5]  
Eliel E.L., 1994, Stereochemistry of Organic Compounds
[6]   Structural order in conjugated oligothiophenes and its implications on opto-electronic devices [J].
Fichou, D .
JOURNAL OF MATERIALS CHEMISTRY, 2000, 10 (03) :571-588
[7]   Bridged triarylamines: A new class of heterohelicenes [J].
Field, JE ;
Hill, TJ ;
Venkataraman, D .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6071-6078
[8]   Synthesis, self-assembly, and nonlinear optical properties of conjugated helical metal phthalocyanine derivatives [J].
Fox, JM ;
Katz, TJ ;
Van Elshocht, S ;
Verbiest, T ;
Kauranen, M ;
Persoons, A ;
Thongpanchang, T ;
Krauss, T ;
Brus, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) :3453-3459
[9]   Search for new allotropic forms of carbon dioxide and carbon disulfide:: A density functional study of CX2-based oligomers (X = O, S) [J].
Frapper, G ;
Saillard, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (22) :5367-5370
[10]   Determination of absolute configuration in molecules with chiral axes by vibrational circular dichroism:: A C2-symmetric annelated heptathiophene and a D2-symmetric dimer of 1,1′-binaphthyl [J].
Freedman, TB ;
Cao, XL ;
Rajca, A ;
Wang, H ;
Nafie, LA .
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (39) :7692-7696