Intramolecular cyclization of triflate/aniline

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SUMMARY

The discussion focuses on the intramolecular cyclization of a molecule containing triflate (-oTf) and aniline (-NH2) moieties, specifically targeting the formation of a secondary amine. Participants suggest using palladium-based catalysts, particularly Pd dba in combination with DPPF, as a viable approach for this reaction. The conversation highlights the lack of existing literature on intramolecular reactions involving these specific functional groups, emphasizing the need for experimental validation of the proposed conditions.

PREREQUISITES
  • Understanding of intramolecular cyclization reactions
  • Familiarity with palladium catalysts, specifically Pd dba
  • Knowledge of ligand interactions, particularly DPPF
  • Basic organic chemistry concepts related to amine and amide formation
NEXT STEPS
  • Research the mechanisms of intramolecular cyclization involving triflates and amines
  • Explore the use of Pd dba and DPPF in various catalytic reactions
  • Investigate alternative catalysts for secondary amine synthesis
  • Review literature on similar reactions to identify potential challenges and solutions
USEFUL FOR

Chemists, particularly those specializing in organic synthesis, researchers exploring catalytic methods for amine production, and graduate students studying reaction mechanisms in organic chemistry.

gravenewworld
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I was wondering if anyone knew of any good catalysts to use for the intramolecular cyclization of a molecule containing -oTf and -NH2 (aniline) moieties. The only references I can find for such reactions between a triflate and an aniline -NH2 only involve 2 separate molecules. Would the same conditions work for an intramolecular rxn?
 
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What product are you after? An amide? A secondary amine?
 
chemisttree said:
What product are you after? An amide? A secondary amine?

Secondary amine.


I was going to try something like Pd dba and DPPF.
 

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