Directed ortho-Metallation in the Presence of a 2,5-Dimethylpyrrole Protecting Group
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This study focuses on the combination ofthe use of a 2,5-dimethylpyrrole protecting group with directed ortho-metallation (DoM) reactions. The 2,5-dimethylpyrrole protecting group was used to prevent the amide from playing a directing role in the metallation reaction. This protecting group was easily and successfully added, and typically removed with reasonable yield. Two directing groups were considered in this study: fluorine and methoxy groups, each of which was reacted with a wide variety of electrophiles. The fluorine directing groups were generally more successful, with better yields and less harsh reaction conditions. Overall, the combination of these two methods was successful, and could easily be extended to make more complex molecules as needed.