Chemical Frustration Opens Synthetic Routes

Chemical Frustration Opens Synthetic Routes

Author: David Bradley

A frustrated Lewis pair is a compound containing a Lewis acid and a Lewis base that, because of steric hindrance, cannot form an adduct. This makes them chemically rather intriguing species that can react with terminal olefins, alkynes, β-H bonds, disulfides, cyclic ethers, carbon dioxide and nitrous oxide.

Now, chemists led by Doug Stephen, University of Toronto, Canada, have demonstrated that they can use phosphine/borane frustrated Lewis pairs to convert cyclopropanes into phosphonium borate products through a ring opening reaction. The products could be used as catalysts for many other synthetic reactions without using metals.

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