Iron oxide mediated direct C–H arylation/alkylation at α-position of cyclic aliphatic ethers

Abstract

We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic aliphatic ethers via activation of C(sp(3))-H. This is the first example of iron oxide mediated direct C-C bond formation without expensive or toxic ligands.

α‐Fe2O3 Nanodisks: Layered Structure, Growth Mechanism, and Enhanced Photocatalytic Property

“…α‐Fe 2 O 3 (hematite) has been extensively investigated. It has been widely used in absorption,3, 4 catalysis18, 19 and lithium‐ion batteries 20–22. Although various α‐Fe 2 O 3 morphologies (nanorods,19 nanowires,23 nanotubes,22, 24 nanosheets,25 and flowers3) have already been fabricated, orientation‐controlled assembly of α‐Fe 2 O 3 is still a challenge.…”

“…We envisioned that such face-to-face assembly would lead to layer-by-layer structured materials, which might have new properties.a-Fe 2 O 3 (hematite) has been extensively investigated. It has been widely used in absorption, [3,4] catalysis [18,19] and lithium-ion batteries. [20][21][22] Although various a-Fe 2 O 3 morphologies (nanorods, [19] nanowires, [23] nanotubes, [22,24] nanosheets, [25] and flowers [3] ) have already been fabricated, orientation-controlled assembly of a-Fe 2 O 3 is still a challenge.…”

Nickel or Phenanthroline Mediated Intramolecular Arylation of sp3 C–H Bonds Using Aryl Halides

“…Pd, Ru, Rh) catalysts and/or expensive phosphine ligands. 1,2 In recent years a number of reports on Cu- 3 and Fe- 4 catalyzed sp 3 C–H bond arylation using heteroarenes 5 or transmetallating reagents 6 have been described. Additionally, an example of Ni-catalyzed intermolecular oxidative arylation of C–H bonds adjacent to ether oxygen or amine nitrogen atoms has been published.…”

Iron‐catalyzed C−H Activation

“…In 2011, Singh's group reported a novel iron oxide‐catalyzed cross‐coupling reaction between organometallic halides and hydrogen‐bearing cyclic ethers such as tetrahydrofuran via direct activation of a C(sp 3 )–H center . In 2012, Weiping et al .…”