Coumaryl Triflate, a Versatile Building Block for the Modification of Coumarins and for Fluorescence Labeling

Abstract

Coumaryl triflate can be used for a wide range of substitution reactions, either under Pd-catalyzed conditions or via direct nucleophilic substitutions, and is therefore an ideal substrate for the fluorescence labeling of functionalized compounds, such as amino acids.

A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols

“…The naphthyl‐coumarin probe 3 was synthesized as shown in Scheme 1. The Suzuki cross coupling reaction of coumaryl triflate 4 with arylboronic acid 5 in the presence of Pd(PPh 3 ) 4 and Na 2 CO 3 gave 6 in 56 % yield [17] . A mixture of POCl 3 in dry DMF was added to a solution of compound 6 in DMF to obtain compound 7 as a yellow solid in 38 % isolated yield.…”

“…The Suzuki cross coupling reaction of coumaryl triflate 4 with arylboronic acid 5 in the presence of Pd(PPh 3 ) 4 and Na 2 CO 3 gave 6 in 56 % yield. [17] A mixture of POCl 3 in dry DMF was added to a solution of compound 6 in DMF to obtain compound 7 as a yellow solid in 38 % isolated yield. The probe 3 was readily prepared by mixing intermediate 7 with 2-(bromomethyl)pyridine hydrobromide in the presence of K 2 CO 3 in dry acetonitrile, arriving at 76 % isolated yield.…”