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Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents

✍ Scribed by J. Klose; A. El-Faham; P. Henklein; L.A. Carpino; M. Bienert

Book ID
104260887
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
209 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the course of comparing the effectiveness of several HOAt-and HOPfp-derived coupling reagents by cyclization and segment condensation of model sequences, using HPLC to follow the time course and to determine the outcome in terms of oligomerization and epimerization, we found a striking improvement of the less effective HOPfp-based coupling reagent (HPyOPfp), both with regard to reaction rate and extent of epimerization, when HOAt was added.

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## Abstract The Suzuki cross‐coupling reaction was employed in the syntheses of eight new [^11^C‐carbonyl]ketones. The reactions between the corresponding boronic acids and the corresponding triflates were performed in the presence of [^11^C]carbon monoxide and a palladium(0) complex as the catalys