10/29/18
Primary amines are essential components of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains a challenge and has so far only been possible through the use of "protective groups". Bill Morandi and his team have now developed a new general strategy that offers access to primary amines from alkenes via a functionally simple iron-catalyzed amino chlorination reaction. It works through the addition of unprotected NH2 from a hydroxylamine derivative directly to a double-bonded carbon center in the presence of table salt (NaCl) as a chloride source. The resulting novel amine derivatives 2-chloroalkylamines have a high reactivity and can be easily converted into a multitude of different, useful amines in asubsequent step. The special feature of the reaction is that it now takes place without "protective groups" and is based on a simple iron catalyst, which fully meets the desire for sustainability.
Bill Morandi's team started research at the amino groups at the Max-Planck-Institut für Kohlenforschung, where Bill Morandi worked as an independent research group leader in the Department of Homogeneous Catalysis until July of this year. In the meantime, the 35-year-old has been appointed at the ETH Zurich as professor at the Laboratory of Organic Chemistry. The article "Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes" was published on 26 October 2018 in Science.