Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.
[reaction: see text] The Suzuki-Miyaura cross-coupling reaction of N,N-dialkylaminomethyltrifluoroborates with aryl halides allows the construction of an aminomethyl aryl linkage through a disconnection based on dissonant reactivity patterns. A variety of these aminomethyltrifluoroborate substrates were prepared in good to excellent yields and then shown to cross-couple with equal facility to both electron-rich and electron-poor aryl halides as well as to a variety of heteroaromatic bromides.
Molander
Gary A
GA
Roy and Diana A. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Sandrock
Deidre L
DL
D000586:Amination; D001881:Borates / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry; D009930:Organic Chemicals / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*
D001881:Borates; D001965:Bromides; D003432:Cross-Linking Reagents; D017672:Nitrogen Compounds; D009930:Organic Chemicals; D011188:Potassium