Stereospecific synthesis of hetero[7]helicenes by Pd-catalyzed double N-arylation and intramolecular O-arylation

被引：165
作者：
Nakano, K
Hidehira, Y
Takahashi, K
Hiyama, T
Nozaki, K
机构：
[1] Univ Tokyo, Dept Chem & Biochem, Grad Sch Engn, Bunkyo Ku, Tokyo 1138656, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 43期
关键词：
arylation; bromination; chirality; helical structures; palladium;
D O I：
10.1002/anie.200502855
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Enantioenriched aza- and oxa[7]helicenes are synthesized from an enantiopure biphenanthryldiol in a highly stereoselective manner. An N-phenylaza[7]helicene is prepared by a palladium-catalyzed double N-arylation of aniline with disulfonate derivatives (see scheme, right), whereas an oxa[7]helicene is obtained by a palladium-catalyzed intramolecular O-arylation of monosulfonate derivatives (see scheme, left). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：7136 / 7138
页数：3
相关论文
共 49 条
[1]   Palladium-catalyzed amination of aryl nonaflates [J].
Anderson, KW ;
Mendez-Perez, M ;
Priego, J ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9563-9573
[2]   SYNTHESIS OF AZONIA DERIVATIVE OF HEXAHELICENE [J].
ARAI, S ;
YAFUNE, T ;
OKUBO, M ;
HIDA, M .
TETRAHEDRON LETTERS, 1989, 30 (51) :7217-7218
[3]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[4]   Efficient asymmetric synthesis of [7]helicene bisquinones [J].
Carreño, MC ;
González-López, M ;
Urbano, A .
CHEMICAL COMMUNICATIONS, 2005, (05) :611-613
[5]   Enantiopure dihydro-[5]-helicenequinones via Diels-Alder reactions of vinyl dihydrophenanthrenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone [J].
Carreño, MC ;
García-Cerrada, S ;
Urbano, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7929-7930
[6]  
CHATTERJ.JN, 1970, J INDIAN CHEM SOC, V47, P576
[7]   Easy synthesis of functionalized hetero[7]helicenes [J].
Dreher, SD ;
Weix, DJ ;
Katz, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3671-3678
[8]   Circularly polarized luminescence from bridged triarylamine helicenes [J].
Field, JE ;
Muller, G ;
Riehl, JP ;
Venkataraman, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11808-11809
[9]   Bridged triarylamines: A new class of heterohelicenes [J].
Field, JE ;
Hill, TJ ;
Venkataraman, D .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6071-6078
[10]  
Flamang-Barbieux M., 1967, TETRAHEDRON LETT, V8, P743, DOI DOI 10.1016/S0040-4039(00)90586-0
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