Iron-Catalyzed 1,4-Addition of α-Olefins to Dienes

Abstract

A new intermolecular, stereo- and regioselective iron-catalyzed 1,4-addition of alpha-olefins to 1,3-dienes using as low as 1 mol % of an iminopyridine-ferrous chloride complex was developed. Importantly, both double bonds of the linear 1,4-diene addition products are obtained with absolute stereocontrol.

Iron Catalysis in Organic Synthesis

“…691 It should be noted that often 1 or 2 mol % of the iron catalyst was sufficient to promote the transformation. 1,4-Dienes were obtained in high yields with complete stereoselectivity for both double bonds.…”

Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes

“…9 In this Communication, we describe the use of analogous, readily prepared iminopyridine-derived iron complexes as catalysts for the regioselective 1,4-addition of pinacolborane (HBPin) to substituted 1,3-dienes (eq 1).…”

Organometallic‐Mediated Radical Polymerization: Developing Well‐Defined Complexes for Reversible Transition Metal‐Alkyl Bond Homolysis

“…For less reactive organic halides, Co, Ni or Fe can be used to activate the RÀX substrate and then transfer R Á to Cr(II), [48] consistent with the higher MÀR homolytic BDE for Cr(III) compared to the other first-row transition metals. The octahedral Cr(III) alkyl complex is remarkably tolerant of functional groups and highly selective for coupling with aldehydes.…”