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Nucleophilic Substitution vs Ring Opening – Dual Reactivity of Benzo[b]phosphol-3-yl Triflates toward Alkyl Grignard Reagents

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A new method for the synthesis of 3-alkylbenzo[ b ]phosphole oxides involving nucleophilic substitution through an addition–elimination mechanism has been developed. The reaction proceeds without a metal catalyst and yields a library of previously unavailable 3-alkylbenzo[ b ]phosphole oxides in yields of up to 90%. This method enables regioselective functionalization at position 3 in the benzophosphole ring, providing the possibility for independent functionalization at both the 3-position and 4–7 positions (benzoring). A competitive ring-opening process that yields 2-ethynylphenyl(alkyl)phosphine oxides and subsequent processes that lead to cyclic side products were also investigated. Mechanistic proposals for all of these processes are presented.

Source: Organometallics

DOI: 10.1021/acs.organomet.5c00193

Authors: Adrianna Maciąg, Łukasz Ponikiewski, Paweł Kubica, Sylwia Sowa

Institutions: Maria Curie-Skłodowska University, Gdańsk University of Technology

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Centre National de la Recherche Scientifique, Politechnika Gdańska, Uniwersytet Marii Curie-Skłodowskiej