Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis
Chengwei Liu, Chong-Lei Ji, Tongliang Zhou, Xin Hong* and Michal Szostak*
*Department of Chemistry, Zhejiang University, Hangzhou 310027, China; Department of Chemistry, Rutgers University, Newark, New Jersey 07102, United States
Email: hxchem
zju.edu.cn, michal.szostakrutgers.edu
C. Liu, C.-L. Ji, T. Zhou, X. Hong, M. Szostak, Org. Lett., 2019, 21, 9256-9261.
DOI: 10.1021/acs.orglett.9b03678
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Abstract
A decarbonylative palladium catalysis enables the synthesis of organophosphorus compounds from ubiquitous aryl and vinyl carboxylic acids. The catalytic system olerates a wide range of functional groups.
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General Procedure for Decarbonylative Phosphorylation of Carboxylic Acids
An ovendried vial equipped with a stir bar was charged with carboxylic acid (neat, 1.0 equiv), diethyl phosphite (neat, typically, 1.0 equiv), Pd(OAc)2 (typically, 5 mol%), ligand (typically, 10 mol%), triethylamine (typically, 1.0 equiv), and trimethylacetic anhydride (typically, 1.0 equiv), placed under a positive pressure of argon, and subjected to three evacuation/backfilling cycles under high vacuum. Dioxane (0.20 M) was added with vigorous stirring at room temperature, the reaction mixture was placed in a preheated oil bath at 160 °C, and stirred for the indicated time at 160 °C. Purification by chromatography on silica gel (EtOAc/hexanes) afforded the title product. EtOAc/hexanes gradient 1:5 to 2:1 for each compound has been used.
Key Words
ID: J54-Y2019
