Efficient carbene transfer reactivity mediated by Fe(II) complexes supported by bulky alkoxides

Area of Science:

• Organometallic Chemistry
• Catalysis
• Organic Synthesis

Background:

• Iron complexes are increasingly explored as sustainable catalysts.
• Carbene transfer reactions are fundamental in organic synthesis.
• Iodonium ylides offer a versatile carbene precursor.

Purpose of the Study:

• To investigate the carbene-transfer reactivity of iron(II) alkoxide complexes.
• To explore the catalytic efficiency of these complexes in cyclopropanation reactions.
• To elucidate the mechanism of iron-catalyzed carbene transfer.

Main Methods:

• Stoichiometric and catalytic reactions with iron(II) alkoxide complexes and iodonium ylides.
• Use of various styrene substrates for cyclopropanation.
• Computational studies and reactivity profiling to probe the reaction mechanism.

Main Results:

• Efficient cyclopropanation of diverse styrenes was achieved using catalytic iron(II) alkoxide precursors.
• The reactions proceeded with high efficiency, demonstrating the utility of the catalytic system.
• A novel remote metallocarbene/vinyl radical intermediate was proposed based on computational and reactivity studies.

Conclusions:

• Iron(II) alkoxide complexes are effective catalysts for carbene transfer reactions.
• The proposed intermediate provides insight into the mechanism of iron-catalyzed cyclopropanation.
• This work expands the scope of iron-based catalysts in organic synthesis.