Palladium-Catalyzed Chemoselective Phosphorylation of Poly(pseudo)halides: A Route for Organophosphorus Synthesis.

Autor: Chen Z; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 000000, Hong Kong SAR, China., Pang WH; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 000000, Hong Kong SAR, China., Yuen OY; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 000000, Hong Kong SAR, China., Ng SS; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 000000, Hong Kong SAR, China., So CM; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 000000, Hong Kong SAR, China.; The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen 518000, P. R. China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Nov 15; Vol. 89 (22), pp. 16262-16268. Date of Electronic Publication: 2024 Feb 12.
DOI: 10.1021/acs.joc.3c02345
Abstrakt: We present an advancement in synthesizing organophosphorus compounds via chemoselective phosphorylation achieved by a palladium and SelectPhos ligand system (Pd/ L1 ). This catalysis system exhibits remarkable chemoselectivity, even in poly(pseudo)halide substrates and overcoming toxicity and substrate scope limitations. The catalytic system is robust, which is demonstrated across diverse substrates such as chloroaryl and bromoaryl triflates. Furthermore, we present a one-pot sequential strategy combining phosphorylation with Suzuki-Miyaura coupling, providing a versatile platform for the efficient synthesis of complex organophosphorus compounds, challenging conventional reactivity paradigms.
Databáze: MEDLINE