ChemIsFun
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Primary amines stable under Suzuki cross-coupling conditions?
Will the -NH2 group of a boronic ester aniline derivative be stable under cross coupling conditions: palladium(0) tetrakistriphenylphosphine, Cs2CO3,
and an aryl bromide? Solvent will likely be iPrOH refluxing and monitored with TLC. Thanks.
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Dr.Bob
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That should work. If you have a stronger base, you could get side reactions, but that should work. If you can deoxygenate the solutions, that will
help a lot. Maybe He, Ar, or N2 to bubble through them before heating to keep the Pd catalyst stable. The nitrogen can complex the catalyst some,
so more Pd may be needed. Better yet to do the reaction with a nitrophenylboronic acid and then reduce, as easier to run, purify, and see on TLC.
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