Barton-McCombie Reaction

Schematic representation of the Barton-McCombie Reaction.

Mechanism of the Barton-McCombie Reaction

Mechanism of the Barton-McCombie Reaction

Original publication	J. Chem. Soc., Perkin Trans. 1. 1975, 16, 1574.
Reviews	Chem. Rev.. 1989, 89, 1413. Comp. Org. Syn.. 1991, 8, 811. Org. React.. 2012, 77, 161. Tetrahedron. 1983, 39, 2609.

Sample reactions

intermediate structure

AIBN, n-Bu3SnH

PhH

Reflux, 4 h, 74%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhH

Reflux, 30 min, 94%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhMe

110 °C, 4 h, 71%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhMe

110 °C, 4 h, 50% (3 steps)

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhMe

72% (3 steps)

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhH

90%

intermediate structure

intermediate structure

n-Bu3SnH

PhMe

Reflux, 6 h, 19%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhMe

Reflux, 2 h, 100%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhH

Reflux, 2 h, 70%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

PhMe

Reflux, 45 min, 66%

intermediate structure

intermediate structure

AIBN, n-Bu3SnH

Dioxane

100 °C, 20 min, 35%

intermediate structure