1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans

Roohollah Kazem Shiroodi, Olesja Koleda, Vladimir Gevorgyan

Journal of the American Chemical Society · 2014 · 94 citations · 49 references

Concepts

Abstract

A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl migration toward C3-borylated furans, whereas employment of the cationic gold hexafluoroantimonate affords C2-borylated furan via a formal 1,2-hydrogen shift.

References

49