Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates.

Molecules

Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

Published: April 2024

AI Article Synopsis

  • An efficient method for synthesizing esters via carbonylation of aryl fluorosulfates and aryl formates was developed, utilizing a palladium catalyst.
  • The reaction produced moderate to good yields of esters and successfully tolerated various functional groups, allowing for further modifications.
  • This process offers a promising alternative to traditional cross-coupling methods that typically use aryl halides and pseudohalides.

Article Abstract

An efficient palladium-catalyzed carbonylation of aryl fluorosulfates with aryl formates for the facile synthesis of esters was developed. The cross-coupling reactions proceeded effectively in the presence of a palladium catalyst, phosphine ligand, and triethylamine in DMF to produce the corresponding esters in moderate to good yields. Of note, functionalities or substituents, such as nitro, cyano, methoxycarbonyl, trifluoromethyl, methylsulfonyl, trifluoromethoxy, fluoro, chloro, bromo, methyl, methoxy, ,-dimethyl, and [1,3]dioxolyl, were well-tolerated in the reactions, which could be kept for late-stage modification. The reactions employing readily available and relatively robust aryl fluorosulfates as coupling electrophiles could potentially serve as an attractive alternative to traditional cross-couplings with the use of aryl halides and pseudohalides as substrates.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11085239PMC
http://dx.doi.org/10.3390/molecules29091991DOI Listing

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