Evidence for a kinetic FLP reaction pathway in the activation of benzyl chlorides by alkali metal-phosphine pairs

Kinetic frustrated Lewis pairs (FLP) allow facile cleavage of a number of E-H bonds (E = H, Si, C, B) where both the Lewis base and Lewis acid are involved in the bond activation transition state. More recently, kinetic FLP systems have been extended to the cleavage of C-X (X = F, Cl, Br) bonds. We...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2024-09, Vol.53 (35), p.14582-14586
Main Authors: Csókás, Dániel, Coles, Max, Toh, Zhi Hao, Young, Rowan D
Format: Article
Language:English
Subjects:
Alkali metals
Cleavage
Ductile-brittle transition
Lewis acid
Lewis base
Phosphines
Sodium
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Summary:Kinetic frustrated Lewis pairs (FLP) allow facile cleavage of a number of E-H bonds (E = H, Si, C, B) where both the Lewis base and Lewis acid are involved in the bond activation transition state. More recently, kinetic FLP systems have been extended to the cleavage of C-X (X = F, Cl, Br) bonds. We report on the role of sodium tetrakis(pentafluorophenyl)borate in the benzylation of triarylphosphines, where the sodium cation and phosphine support a kinetic FLP type transition state. The presence of Na + is found to accelerate Bn−Cl bond cleavage by PPh 3 via a kinetic frustrated Lewis pair (FLP) pathway.
ISSN:1477-9226
1477-9234
1477-9234
DOI:10.1039/d4dt02028f