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Suzuki Coupling. Mechanism of Suzuki Coupling. Gabriel Synthesis. Notice that the phthalimide moiety serves as a ‘protected’ form of ammonia. The phthalimide carbonyls increase the acidity of the nitrogen (thus allowing formation of its conjugate base)

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Gabriel synthesis
Gabriel Synthesis

Notice that the phthalimide moiety serves as a ‘protected’ form of ammonia.

The phthalimide carbonyls increase the acidity of the nitrogen (thus allowing formation of its conjugate base)

Most importantly, the phthalimide carbonyls protect the nitrogen form ‘over alkylation’ thus preventing the formation of secondary and tertiary amines (and quaternary ammonium salts).



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