Intertwined chemistry of hydroxyl hydrogen-bond donors, epoxides and isocyanates in the organocatalytic synthesis of oxazolidinones versus isocyanurates: rational catalytic investigation and mechanistic understanding

Abstract

<p>Hydroxyl compounds represent an important family of organocatalysts with the ability to coordinate and activate the reaction substrates by establishing an array of hydrogen bonds. Thus far, the use of...</p>

Recent progress in the catalytic transformation of carbon dioxide into biosourced organic carbonates

“…301 In order to better exploit the generally assumed benefits of organocatalysis (lower catalyst cost and toxicity), the application of ubiquitous biobased compounds such as amino acids, 302,303 peptides, [304][305][306] sugars, 307 and vitamins, 308 would be highly attractive. 309 In this context, L-ascorbic acid (14), a well-established biobased HBD for the cycloaddition of heterocumulenes to epoxides under ambient or mild conditions, 310,311 was applied in combination with TBAC for the cycloaddition of CO 2 to iEFAs. 231 Ascorbic acid was found to accelerate the quaternary ammonium salt-catalyzed cycloaddition of CO 2 to iEFA1, with the binary combination 14/TBAC showing the best performance in terms of iCFA1 selectivity (see also Table 3).…”

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

“…Yingcharoen and co‐workers employed ascorbic acid as a hydrogen‐bonding donor catalyst in the binary organocatalytic system (Scheme 18). 40 The coupling reactions of epoxides and aryl isocyanates efficiently proceeded under the binary organocatalytic system using ascorbic acid and tetrabutylammonium iodide. The target 2‐oxazolidinones 1 were obtained in moderate to good yields under the binary organocatalytic system.…”

Crosslinked porous polyimides: structure, properties and applications

“…In particular, recent focus has been placed on the direct conversion of CO 2 to useful chemicals (rather than storage). 130,131 For instance, robust and moisture-insensitive pPIs incorporating functional groups such as hydrogen-bond donors, 132,133 nucleophilic species such as pyridines, 134,135 or Lewis acidic metal centres 136,137 could serve as components of catalytic systems for the direct conversion of CO 2 and epoxides to cyclic carbonates. Further opportunities in energy conversion and storage (as touched on in Section 4.2 focusing on photocatalysis) are also available for further significant effort and exploitation.…”