Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source.
A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN(3) as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN(3) to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.
Zhao
Haibo
H
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China.
Fu
Hua
H
Qiao
Renzhong
R
D000577:Amides / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D019810:Sodium Azide / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; D001565:Benzoates; D003300:Copper; D019810:Sodium Azide