Sustainable C(sp3)-H Bond Functionalization by Jin Xie & Chengjian Zhu

Author:Jin Xie & Chengjian Zhu
Language: eng
Format: epub
Publisher: Springer Berlin Heidelberg, Berlin, Heidelberg

Iron catalysis is an emerging branch in metal-catalyzed coupling strategies. In 2010, Jiao et al. accomplished the first Fe(II)-catalyzed allylic C–H oxidation to alkenyl nitriles with TMSN3 as nitrogen source and DDQ as external oxidant [139]. As a follow-up work, the same group developed FeCl2-catalyzed oxidative, dehydrogenative C–O coupling of propargyl azides with carboxylic acids in the presence of DDQ [140]. The authors envisioned that azido moiety would be an assisting group for specific allylic C–H bond activation.

It is noteworthy that the first Fe(acac)3-catalyzed non-oxidative allylic C–H arylation with commercially available aryl Grignard reagents was achieved by Nakamura et al. in 2013 (Scheme 2.27). [141] The mechanistic study indicates allylic C(sp3)–H bond activation to form an allyliron species 7 is the rate-determining step during the reaction process. The future efforts will focus on detailed mechanism studies.

Scheme 2.27Fe-catalyzed redox-neutral allylic C(sp3)–H arylation [141]

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