A Common Diaryl Ether Intermediate for the Gram-Scale Synthesis of Oxazine and Xanthene Fluorophores

被引:36
作者
Anzalone, Andrew V. [1 ]
Wang, Tracy Y. [1 ]
Chen, Zhixing [1 ]
Cornish, Virginia W. [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
copper; cyclization; domino reaction; dyes/pigments; fluorescence; FLUORESCENT-PROBE; ARYL HALIDES; SUPERRESOLUTION; RHODAMINES; CHEMISTRY;
D O I
10.1002/anie.201205369
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Common ground: Copper-catalyzed coupling reactions can be used for the high-yielding preparation of widely used oxazine and xanthene fluorophores from a common diaryl ether intermediate on a gram-scale (see scheme). This general approach may facilitate the future development of novel fluorophores and probes with unique properties. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:650 / 654
页数:5
相关论文
共 33 条
[11]   REACTIONS OF SODIUM-BOROHYDRIDE IN ACIDIC MEDIA .1. REDUCTION OF INDOLES AND ALKYLATION OF AROMATIC-AMINES WITH CARBOXYLIC-ACIDS [J].
GRIBBLE, GW ;
LORD, PD ;
SKOTNICKI, J ;
DIETZ, SE ;
EATON, JT ;
JOHNSON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7812-7814
[12]  
GRYNKIEWICZ G, 1985, J BIOL CHEM, V260, P3440
[13]  
Haidekker MA, 2006, J AM CHEM SOC, V128, P398, DOI 10.1021/ja056370a
[14]  
Heilemann M., 2009, Angew. Chem, V121, P7036
[15]   Super-Resolution Imaging with Small Organic Fluorophores [J].
Heilemann, Mike ;
van de Linde, Sebastian ;
Mukherjee, Anindita ;
Sauer, Markits .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) :6903-6908
[16]   Super-Resolution Fluorescence Microscopy [J].
Huang, Bo ;
Bates, Mark ;
Zhuang, Xiaowei .
ANNUAL REVIEW OF BIOCHEMISTRY, 2009, 78 :993-1016
[17]  
Kanitz A, 1999, EUR J ORG CHEM, V1999, P923, DOI 10.1002/(SICI)1099-0690(199904)1999:4<923::AID-EJOC923>3.0.CO
[18]  
2-N
[19]   Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction [J].
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14844-14845
[20]  
Kobayashi S, 2001, ADV SYNTH CATAL, V343, P71, DOI 10.1002/1615-4169(20010129)343:1<71::AID-ADSC71>3.3.CO