Organic Letters 2007-04-12

Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Gary A Molander, Deidre L Sandrock

Index: Org. Lett. 9 , 1597, (2007)

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Abstract

[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.