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

We report a dual photoredox and hydrogen atom transfer (HAT) catalysed α-C-H alkylation of unprotected, aliphatic primary amines with diphenyl(vinyl)phosphine oxide. This simple protocol, which can be run on gram-scale in continuous flow, enables the direct synthesis of γ-amino phosphine oxide building blocks. By condensation with aromatic aldehydes and base-induced 5-endo-trig cyclisation, the latter compounds can be converted into α-arylated, spirocyclic pyrrolidines. Finally, we show that attempted deprotonation of γ-amino phosphine oxides with strong base leads to an unexpected cyclisation to afford cyclic phosphinamide products.

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

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

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