Intramolecular cyclization of triflate/aniline

  • Thread starter gravenewworld
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In summary, intramolecular cyclization of triflate/aniline is a chemical reaction that involves the ring closure of a triflate group and an aniline group within the same molecule. The mechanism involves the triflate group acting as a nucleophile and displacing a leaving group, leading to the formation of a key intermediate. This reaction has various applications in organic synthesis and can be influenced by factors such as steric hindrance and reaction conditions. Other functional groups besides triflate and aniline can also be used in intramolecular cyclization reactions, making it a versatile tool for the synthesis of cyclic compounds.
  • #1
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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  • #2
What product are you after? An amide? A secondary amine?
 
  • #3
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.
 

1. What is intramolecular cyclization of triflate/aniline?

Intramolecular cyclization of triflate/aniline is a chemical reaction in which a triflate group (CF3SO3-) and an aniline group (C6H5NH2) within the same molecule undergo a ring closure to form a cyclic compound.

2. What is the mechanism of intramolecular cyclization of triflate/aniline?

The mechanism of intramolecular cyclization of triflate/aniline involves the triflate group acting as a nucleophile, attacking the aniline group and displacing a leaving group. This leads to the formation of a key intermediate, which then undergoes a series of proton transfers and elimination reactions to form the final cyclic product.

3. What are the applications of intramolecular cyclization of triflate/aniline?

Intramolecular cyclization of triflate/aniline is commonly used in organic synthesis to construct complex cyclic compounds, such as heterocycles. These compounds have a wide range of applications in the pharmaceutical, agrochemical, and materials industries.

4. What factors influence the efficiency of intramolecular cyclization of triflate/aniline?

The efficiency of intramolecular cyclization of triflate/aniline can be influenced by several factors, including the steric hindrance of the reactants, the nature of the solvent, and the reaction conditions (e.g. temperature, catalyst). Additionally, the stability of the intermediate and the ability of the leaving group to leave also play important roles.

5. Can other functional groups besides triflate and aniline be used in intramolecular cyclization reactions?

Yes, other functional groups such as alcohols, carboxylic acids, and amines can also be used in intramolecular cyclization reactions. These reactions are highly versatile and can be tailored to incorporate a variety of functional groups, allowing for the synthesis of a diverse range of cyclic compounds.

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