Amide Bond Formation with a New Fluorous Carbodiimide:  Separation by Reverse Fluorous Solid-Phase Extraction

A new fluorous carbodiimide is introduced along with a convenient procedure for amide coupling reactions. Reactions of acids and amines under standard conditions for carbodiimide couplings, followed by simple reverse fluorous solid-phase extraction (FSPE) over standard silica gel, provide the target...

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Bibliographic Details
Published in:Organic letters 2007-10, Vol.9 (21), p.4167-4170
Main Authors: del Pozo, Carlos, Keller, Adam I, Nagashima, Tadamichi, Curran, Dennis P
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - chemistry
Amines - chemistry
Carbodiimides - chemical synthesis
Carbodiimides - chemistry
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
Solid Phase Extraction - instrumentation
Solid Phase Extraction - methods
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Summary:A new fluorous carbodiimide is introduced along with a convenient procedure for amide coupling reactions. Reactions of acids and amines under standard conditions for carbodiimide couplings, followed by simple reverse fluorous solid-phase extraction (FSPE) over standard silica gel, provide the target amide products in good yields and purities. The use of HFE-7100 as a fluorous solvent is crucial for the success of the reverse FSPE.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701631m