Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines

Giang D. Vo and John F. Hartwig*

*Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, Email: jhartwiguiuc.edu

G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc., 2009, 131, 11049-11061.

DOI: 10.1021/ja903049z

---

see article for more reactions

Abstract

A complex generated from Pd[P(o-tol)₃]₂ and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates. The couplings with this catalyst conducted with a solution of ammonia in dioxane form primary arylamines from various aryl electrophiles in high yields.

see article for more examples

---

---

Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent

S. Lee, M. Jørgensen, J. F. Hartwig, Org. Lett., 2001, 3, 2729-2732.

Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts

R. A. Green, J. F. Hartwig, Org. Lett., 2014, 16, 4388-4391.

[(CyPF-tBu)PdCl₂]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides

Q. Sheng, J. F. Hartwig, Org. Lett., 2008, 10, 4109-4112.

---

Key Words

Buchwald-Hartwig Coupling, Anilines

---

ID: J48-Y2009-2420