Fluorous-tagged carbamates for the pd-catalyzed amination of aryl halides.
A novel fluorous-tagged ammonia surrogate has been synthesized and its application to the synthesis of anilines by Buchwald-Hartwig palladium-catalyzed amidation-hydrolysis protocol is described. Primary anilines were obtained in moderate to good yields after a sequence of two reaction steps involving fluorous separation techniques for their purification. Preliminary results indicate that N-substituted anilines can also be obtained using just N-substituted-FBoc carbamates as the nitrogen source.
Trabanco
Andrés A
AA
Johnson and Johnson Pharmaceutical Research and Development, Research and Early Development Europe, CNS-Psychiatry, Division of Janssen-Cilag, Medicinal Chemistry Department, Jarama 75, 45007 Toledo, Spain. atrabanc@prdes.jnj.com
Vega
Juan A
JA
Fernandez
M Alejandro
MA
D000586:Amination; D000641:Ammonia / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001577:Benzophenones / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D005563:Formic Acid Esters / Q000138:chemical synthesis / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000814:Aniline Compounds; D001577:Benzophenones; D002219:Carbamates; D005563:Formic Acid Esters; D006841:Hydrocarbons, Aromatic; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; C000345:t-butyloxycarbonyl group; D010165:Palladium; C047723:benzophenone; D000641:Ammonia