Photoredox-HAT catalysed α-C-H alkylation of primary amines with vinyl phosphine oxides: New building blocks for spiropyrrolidine synthesis

A dual photoredox and hydrogen atom transfer (HAT) catalysed α-C–H alkylation of unprotected, aliphatic primary amines with diphenyl(vinyl)phosphine oxide has been developed. This straightforward protocol, which can be carried out on gram scale in continuous flow, enables the direct synthesis of γ-amino phosphine oxide building blocks. Condensation with aromatic aldehydes, followed by base-induced 5-endo-trig cyclisation, is employed to afford α-arylated, spirocyclic pyrrolidines. Finally, it has been shown that attempted deprotonation of γ-amino phosphine oxides with strong base is accompanied by an unexpected cyclisation, through which cyclic phosphinamide products are formed.

• Kinsella, A
• Bell-Tyrer, J
• Stead, D
• Cresswell, A

• Department of Chemistry, University of Bath, 1 South, Claverton Down, Bath, BA2 7AY, UK

• Request a Brochure
• Request more Info
• Request a Quote