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Seminar
Subject: Fluorescence Resonance Energy Transfer (FRET) as a High-Throughput
Assay for Coupling Reactions. Arylation of Amines as a Case Study.
Authors: Shaun R. Stauffer and John F. Hartwig*.
Source: J. Am. Chem. Soc. 2003, 125, 6977-6985.
Speaker: B89203014 化學四 王大明
Date: 03 / 23 / 2004
Abstract: A solution-phase assay based on fluorescence resonance energy
transfer (FRET) was developed for high-throughput screening of palladium
catalyzed aminations of aryl halides. Dansylpiperazine was used as the
fluorescent component and a chloro- or bromoarene tagged with an azodye as the
quenching partner. A library of 119 phosphine and heterocyclic carbene ligands
was evaluated in duplicate reactions of two combinations. In general, the FRET
assay displayed excellent reproducibility, with less than 5% of the duplicate
experiments showing significant variability in yields. The reaction yields
obtained by the FRET method were reproducible and agreed in most cases with
yields obtained by conventional methods. In addition to an evaluation of the
accuracy of the FRET assay, this work includes the use of the FRET assay to
investigate relative activities of various catalysts for the amination of aryl
bromides and chlorides and to find conditions for aminations in more polar
solvents. Reactions with K3PO4 base in aqueous mixtures of polar and nonpolar
organic solvents were shown to be appropriate for the amination chemistry.
Overall, this work shows that FRET can be used to screen homogeneous catalysts
for the amination of aryl halides and, by analogy, to screen catalysts for
other processes.
References:
(1) Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13.
(2) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
(3) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S.; Hartwig, J. F. Org.
Lett. 2000, 9, 1423-1426.
(4) Grasa, G. A.; Viciu, M. S.; Huang, J. K.; Nolan, S. P. J. Org. Chem. 2001,
66, 7729-7737.
(5) Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132
(6) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J. J.; Buchwald, S. L. J.
Org. Chem. 2000, 65, 1158-1174.
(7) Lakowicz, J. R. Principles of Flurescence Spectroscopy, 1999, 367-374.
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在準備這篇paper時才發現內容比我上學期的還難
上學期有人曾說完全不知道我講的什麼...
不知這次...
希望星期二上台講的時候不要變成大家都不知道我在說什麼...
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