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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 02期

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

页码：650 / 654

页数：5

共 33 条

[11] REACTIONS OF SODIUM-BOROHYDRIDE IN ACIDIC MEDIA .1. REDUCTION OF INDOLES AND ALKYLATION OF AROMATIC-AMINES WITH CARBOXYLIC-ACIDS
GRIBBLE, GW
LORD, PD
SKOTNICKI, J
DIETZ, SE
EATON, JT
JOHNSON, JL
[J]. 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
Heilemann, Mike
van de Linde, Sebastian
Mukherjee, Anindita
Sauer, Markits
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6903 - 6908
[16] Super-Resolution Fluorescence Microscopy
Huang, Bo
Bates, Mark
Zhuang, Xiaowei
[J]. 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
Klapars, A
Buchwald, SL
[J]. 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

← 1 2 3 4 →