Chemoselectivity in the cationic Phospha-Wittig reaction: accessing phosphorus heterocycles, phosphaalkenes, and their annulated [4 + 2] dimers.

ABSTRACT: Triflate salts of phosphito-phosphanides [L_CP-P(OR)₃]⁺ (1[OTf], R = alkyl, L_C = N-heterocyclic carbene) were obtained via nucleophilic fragmentation of the tetraphosphetane [(L_C)₄P₄][OTf]₄ (3[OTf]₄) with organophosphites P(OR)₃. The salts 1[OTf] act as versatile reagents in the cationic Phospha-Wittig reaction, converting aldehydes into imidazoliumyl-substituted phosphaalkenes 2[OTf] and, via a competing pathway, into diphosphiranes 4[OTf]₂. The product distribution is governed by the aldehyde substituent, enabling selective access to isolable derivatives of both compound classes. The resulting phosphaalkenes 2[OTf] serve as precursors to diverse pho

SUBMITTER: Royla P 

PROVIDER: S-EPMC12797139 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature