open access

https://hdl.handle.net/2115/97996

Synthesis of imidoyltrialkylphosphonium salts through photocatalytic reactions between isocyanides and tri-t-butylphosphine

英語

photoredox catalysis

2025-07-09

Oxford University Press

Chemistry letters

54(7)

Isocyanides and tri-t-butylphosphine undergo a C-P bond-forming reaction under photocatalytic conditions. The resulting imidoyltrialkylphosphonium salts represent a new class of organophosphorus compounds that can be isolated by silica gel chromatography under air. This transformation exhibits broad functional group tolerance and affords a range of imidoylphosphonium salts in good to moderate yields. Mechanistic studies suggest a reaction pathway involving addition of a phosphine radical cation to the isocyanide, followed by single-electron reduction to form a phosphorus ylide intermediate. Furthermore, the imidoylphosphonium salts exhibit unique reactivity under reductive conditions, enabling their conversion to imidoylphosphines through elimination of a P-substituent.

学術雑誌論文

Accepted Manuscript

This is a pre-copyedited, author-produced version of an article accepted for publication in Chemistry letters following peer review. The version of record Ayaka Sakurada, Masaya Sawamura, Yusuke Masuda, Synthesis of imidoyltrialkylphosphonium salts through photocatalytic reactions between isocyanides and tri-t-butylphosphine, Chemistry Letters, Volume 54, Issue 7, July 2025, upaf134, https://doi.org/10.1093/chemle/upaf134 is available online at: https://doi.org/10.1093/chemle/upaf134.

0366-7022