The Barton–McCombie Reaction is an organic reaction in which a hydroxyl functional group in an organic compound is replaced by a hydrogen atom, forming an alkane. This reaction was discovered in 1975 by British chemists Derek Harold Richard Barton and Stuart W. McCombie, and is named after them. It is one of the effective methods for deoxygenation of alcohols.

Reagents: AIBN, tributyltin hydride (Bu₃SnH)
Reactants: Alcohols
Products: Alkanes
Reaction Type: Substitution reaction (radical substitution)

Experimental Tips:

• In addition to thioacyl chlorides, other thionocarbonyl reagents can also be used in the reaction, such as 1,1'-thiocarbonyldiimidazole (TCDI).

• The traditional method uses toxic and expensive tributyltin hydride.

• To address this issue, more environmentally friendly and cost-effective alternatives have been developed, such as using tributyltin oxide as the radical source and polymethylhydrosiloxane (PMHS) as the hydrogen donor.

Reaction Mechanism

Original Reference:
Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1, 1975, 1574–1585.

Popular Citations:

• Bu₃SnH-Catalyzed Barton−McCombie Deoxygenation of Alcohols. J. Am. Chem. Soc., 1997, 119(29), 6949–6950.

• Reflections on the Mechanism of the Barton–McCombie Deoxygenation and on its Consequences. Tetrahedron, 2018, 74(38), 4969–4979.