Abstract

In this review, the progress made in the palladium-catalyzed amination of aryl halides and sulfonates is described with particular attention given to applications in synthetic organic chemistry.

Author Keywords: Anilines; N-Aryl amines; Palladium catalysts; Phosphine ligands

Article Outline

1. Introduction

2. Background and outline

3. N-Arylation of secondary amines

3.1. Cross-coupling of acyclic amines with aryl bromides

3.2. Cross-coupling of acyclic amines with aryl chlorides

3.3. Cross-couplings of acyclic amines with aryl triflates

3.4. Cross-coupling of cyclic amines with aryl bromides

3.5. Cross-couplings of cyclic amines with aryl chlorides

3.6. Cross-couplings of cyclic amines with aryl triflates

4. N-Arylation of primary amines

4.1. Cross-couplings of aliphatic amines with aryl bromides and iodides

4.2. Cross-coupling of aliphatic amines with aryl chlorides

4.3. Cross-coupling of aliphatic amines with aryl sulfonates

4.4. Cross-coupling of primary anilines with aryl bromides and iodides

4.5. Cross-coupling of anilines with aryl chlorides

4.6. Cross-coupling of anilines with aryl sulfonates

5. N-Arylation of ammonia surrogates

6. N-Arylation of other nitrogen-containing substrates

7. Intramolecular N-arylation reactions

8. Conclusions

Acknowledgements

References

*1 Dedicated to Professors Richard Heck and Jiro Tsuji in recognition of their manifold pioneering contributions to the field of organopalladium chemistry.

Corresponding author. Fax: +1-617-2533297; email: sbuchwal@mit.edu