CO<sub>2</sub> and palladium enabled highly chemoselective hydroxylation of <i>gem</i>-difluorocyclopropanes

Wang, Xingben; Xiao, Fang; Patureau, Frederic W.

doi:10.1039/d4qo00106k

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00106k

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CO₂ and palladium enabled highly chemoselective hydroxylation of gem-difluorocyclopropanes

Xingben Wang,

Fang Xiao,

Frederic W. Patureau

Abstract: The CO2-mediated hydroxylation of gem-difluorocyclopropanes is herein described, under Pd(0) catalysis in the presence of H2O. The method affords a large series of valuable fluorinated cinnamyl alcohols in high yields...

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Cited by 5 publications

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Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

Su,

Qian,

Wen

et al. 2024

Asian J Org Chem

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Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

Su,

Qian,

Wen

et al. 2024

Asian J Org Chem

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CO₂‐Promoted Reactions: A Prosperous Strategy for Conversion of Functional Group in Organic Synthesis

Zhang,

2024

ChemCatChem

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Due to its non‐toxic nature, cost‐effectiveness, and natural abundance, carbon dioxide (CO2) is increasingly recognized as a valuable C1 source in organic synthesis. In addition to the building block for molecular construction, the role of CO2 as a promoter or catalyst to enhance reaction rates and selectivity is gaining attention. Acting as a reversible covalent Lewis acid, CO2 can function as an activating group in the transformation of various compounds, such as alcohols and amines, facilitating the dissociation of hydroxyl or activation of amino. It can also modulate the reactivity of nucleophilic reagents, including H2O, N‐heterocyclic carbenes (NHCs), cyanide (CN), and nucleophilic reductants like borohydride (BH4‐). When CO2 interacts with these nucleophiles, it can exhibit Brønsted acidity or hydrogen‐bond donating capabilities and can also act as a coordinating ligand to transition metals in its carboxylate form (‐CO2‐). In this review, we mainly summarize and classify the synthetic applications and mechanistic insights of CO2‐promoted reactions according to different functional groups and bonding types, which include: CO2‐promoted functional transformation of alcohols; CO2‐promoted functional transformation of amines; CO2–promoted reactions in protic solvent; CO2‐promoted reactions via adducts of CO2 and nucleophiles; CO2‐promoted reductive reaction.

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Oxidative N−N Bond Formation Versus the Curtius Rearrangement

Hohenadel,

Ebel,

Oppel

et al. 2024

Chemistry A European J

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The oxidative formation of N–N bonds from primary amides has been recently reported and then retracted in the journal Nature Communications by Kathiravan, Nicholls, and coauthors, utilizing a hypervalent iodane reagent. Unfortunately, the authors failed to recognize the Curtius reaction taking place under the described reaction conditions. Thus, the claimed N–N coupling products were not formed. Instead, the Curtius rearrangement urea coupling products were obtained. We demonstrate this herein by means of NMR and x‐ray analysis, as well as with the support of an alternative synthetic route.

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CO₂ and palladium enabled highly chemoselective hydroxylation of gem-difluorocyclopropanes

Abstract: The CO2-mediated hydroxylation of gem-difluorocyclopropanes is herein described, under Pd(0) catalysis in the presence of H2O. The method affords a large series of valuable fluorinated cinnamyl alcohols in high yields...

Cited by 5 publications

References 78 publications

Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

CO₂‐Promoted Reactions: A Prosperous Strategy for Conversion of Functional Group in Organic Synthesis

Oxidative N−N Bond Formation Versus the Curtius Rearrangement

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CO2 and palladium enabled highly chemoselective hydroxylation of gem-difluorocyclopropanes

Abstract: The CO2-mediated hydroxylation of gem-difluorocyclopropanes is herein described, under Pd(0) catalysis in the presence of H2O. The method affords a large series of valuable fluorinated cinnamyl alcohols in high yields...

Cited by 5 publications

References 78 publications

Pd/IPrBIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

Pd/IPrBIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

CO2‐Promoted Reactions: A Prosperous Strategy for Conversion of Functional Group in Organic Synthesis

Oxidative N−N Bond Formation Versus the Curtius Rearrangement

Contact Info

Product

Resources

About

CO₂ and palladium enabled highly chemoselective hydroxylation of gem-difluorocyclopropanes

Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

Pd/IPr^BIDEA‐Catalyzed Synthesis of Pyrroles via Cascade C−C/C−F Cleavage/Annulation of gem‐Difluorocyclopropanes

CO₂‐Promoted Reactions: A Prosperous Strategy for Conversion of Functional Group in Organic Synthesis