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Chemistry · L5 · Metal-Catalyzed Diazo Decomposition to a Carbenoid

How a Rh(II) or Cu catalyst decomposes a diazo compound by expelling N2 to form a metal carbenoid, which then transfers its carbene unit to an alkene (cyclopropanation) or a C-H bond (insertion) under chiral ligand control.

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Diazo compound R2C=N2Metal-diazo adductMetal carbenoid: electrophilic carbene stabilized by metalCyclopropanation: carbene transferred to alkene pi bondC-H insertion: carbene inserts into C-H bondChiral ligand environment controls facial selectivityEnantioenriched product, catalyst regeneratedCoordinates to metal catalystLoses N2 gasEncounters alkeneEncounters C-H bond

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