Marko-Lam Deoxygenation

• General Characteristics

The deoxygenation of alcohols via p-toluic acid esters under single-electron reduction conditions is known as the Marko-Lam deoxygenation.

It has advantages over the Barton-McCombie deoxygenation, including higher stability of the precursors, faster and milder reaction conditions, and unnecessity of toxic (and difficult to remove) organic tin reagents.

• General References

Lam, K.; Marko I.E. Org. Lett. 2008, 10, 2773. DOI: 10.1021/ol800944p

Lam, K.; Marko I.E. Chem. Comm. 2009, 95. DOI: 10.1039/b813545b

Lam, K.; Marko I.E. Org. Lett. 2009, 11, 2752. DOI: 10.1021/ol900828x

Lam, K.; Marko I.E. Tetrahedron 2009, 65, 10930. doi:10.1016/j.tet.2009.09.111

• Reaction Mechanism

The resulting alkyl radical intermediate can be subjected to further reactions such as cyclization.

• Examples

• Experimental Procedure

• Experimental Tips

• References

• Related Reactions

Reductive Desulfurization

Intramolecular Radical Cyclization

 Movassaghi Deoxigenation

Hunsdiecker Reaction

Barton Decarboxylation

 Kagan-Molander Coupling

 Barton-McCombie Deoxygenation

Conversion from Alcohol to Alkane

• Related Books

• External Links

Marko-Lam Deoxygenation – Wikipedia

Alkane synthesis by deoxygenation (organic-chemistry.org)

Lam Kevin: CV

 

deoxygenation, para-toluyl ester, samarium iodide