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Cavitand‐Based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
Author(s) -
MartínezRodríguez Luis,
Otalora Garmilla Javier,
Kleij Arjan W.
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201501463
Subject(s) - resorcinol , pyrogallol , chemistry , cavitand , catalysis , reactivity (psychology) , organic chemistry , organocatalysis , aldehyde , polyphenol , intermolecular force , combinatorial chemistry , reagent , enantioselective synthesis , molecule , antioxidant , supramolecular chemistry , medicine , alternative medicine , pathology
A variety of cavitand‐based polyphenols was prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents to give the respective resorcin[4]‐ or pyrogallol[4]arenes. The preorganization of the phenolic units allows intra‐ and intermolecular hydrogen bond (HB) networks that affect both the reactivity and stability of these HB‐donor catalysts. Unexpectedly, we found that the resorcin[4]arenes show cooperative catalysis behavior compared to the parent resorcinol in the catalytic coupling of epoxides and CO 2 with a significantly higher turnover. At elevated reaction temperatures, the resorcin[4]arene‐based catalyst 3 d displays the best catalytic performance with very high turnover numbers and frequencies, combining increased reactivity and stability compared to pyrogallol, and an ample substrate scope. This type of polyphenol structure thus illustrates the importance of a new, highly competitive organocatalyst design to devise sustainable CO 2 conversion processes.