Taming the Reactivity of Phosphiranium Salts: Site-Selective C-Centered Ring Opening for Direct Synthesis of Phosphinoethylamines

Julien Gasnot; Clément Botella; Sébastien Comesse; Sami Lakhdar; Carole Alayrac; Annie-Claude Gaumont; Vincent Dalla; Catherine Taillier

doi:10.1002/anie.201916449

Taming the Reactivity of Phosphiranium Salts: Site-Selective C-Centered Ring Opening for Direct Synthesis of Phosphinoethylamines

Angew Chem Int Ed Engl. 2020 Jul 13;59(29):11769-11773. doi: 10.1002/anie.201916449. Epub 2020 May 18.

Authors

Julien Gasnot¹, Clément Botella¹, Sébastien Comesse¹, Sami Lakhdar², Carole Alayrac², Annie-Claude Gaumont², Vincent Dalla¹, Catherine Taillier¹

Affiliations

¹ Normandie Univ., URCOM, UNIHAVRE, FR 3032, EA 3221, 25 rue Philippe Lebon, BP 540, 76058, Le Havre, France.
² Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6, Boulevard Marechal Juin, 14000, Caen, France.

PMID: 32240563
DOI: 10.1002/anie.201916449

Abstract

Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three-chain-atom electrophilic building blocks. Notably, control of their challenging C-centered electrophilicity is disclosed with an expedient synthesis of tertiary β-anilino phosphines as a proof-of-concept.

Keywords: nucleophilic ring opening; phosphinoethyl amines; phosphiranium ions; selectivity; steric protection.

Grants and funding

Région Normandie, Réseau Crunch