Three-component reaction of amines, epoxides, and carbon dioxide: A straightforward route to organic carbamates

Hosseinian, Akram; Ahmadi, Sheida; Mohammadi, Robab; Monfared, Aazam; Rahmani, Zahra

doi:10.1016/j.jcou.2018.08.013

Cited by 53 publications

(25 citation statements)

References 52 publications

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“…Another challenging task was the research of organocatalysts as efficient as metal catalysts. In these cases, the intervention of hydrogen bond donors in the catalyst is often necessary to activate the ring opening step (see entries 24,25,27,29,34,35,37,38,39,40,44,45,46,62,66,69,70). Very recently, the activity of a diverse selection of hydrogen bond donors has been correlated to their pK a [119].…”

Section: Cyclic Carbonatesmentioning

confidence: 99%

“…Therefore, the development of new methods for their synthesis is always welcome in the chemical community, in particular if these methods benefit from cheap, simple, and readily available starting materials. Notwithstanding the strong effort of Vessally [28][29][30][31][32][33] and others [34][35][36][37] to review large part of the synthesis of heterocycles by CO 2 fixation, many papers appeared in the literature in the last years, making an update necessary. Therefore, this review aims to summarize and discuss the recent advances in the reaction of CO 2 , for the synthesis of cyclic carbonates, carbamates, and ureas.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

et al. 2019

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Carbon dioxide produced by human activities is one of the main contributions responsible for the greenhouse effect, which is modifying the Earth’s climate. Therefore, post-combustion CO2 capture and its conversion into high value-added chemicals are integral parts of today’s green industry. On the other hand, carbon dioxide is a ubiquitous, cheap, abundant, non-toxic, non-flammable and renewable C1 source. Among CO2 usages, this review aims to summarize and discuss the advances in the reaction of CO2, in the synthesis of cyclic carbonates, carbamates, and ureas appeared in the literature since 2017.

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Section: Cyclic Carbonatesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

et al. 2019

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“…Reactions of aziridines, [99][100][101] propargylic amines,a llylic amines and 1,2-aminoalcohols with CO 2 yield oxazolidinones and their derivatives (Scheme 12) [102][103][104][105][106][107] and six-membered oxazin-2-ons from allenic amines [108,109] or 2-ethynylaniline (Scheme 13). [110] 2-Ethynylanilines are isostructural with 2- Figure 14.…”

Section: Cyclic Carbamatesmentioning

confidence: 99%

Pivotal Role of the Basic Character of Organic and Salt Catalysts in C−N Bond Forming Reactions of Amines with CO₂

Hulla

Dyson

2019

Angew Chem Int Ed

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Organocatalysts promote a range of C−N bond forming reactions of amines with CO2. Herein, we review these reactions and attempt to identify the unifying features of the catalysts that allows them to promote a multitude of seemingly unrelated reactions. Analysis of the literature shows that these reactions predominantly proceed by carbamate salt formation in the form [BaseH][RR′NCOO]. The anion of the carbamate salt acts as a nucleophile in hydrosilane reductions of CO2, internal cyclization reactions or after dehydration as an electrophile in the synthesis of urea derivatives. The reactions are enhanced by polar aprotic solvents and can be either promoted or hindered by H‐bonding interactions. The predominant role of all types of organic and salt catalysts (including ionic liquids, ILs) is the stabilization of the carbamate salt, mostly by acting as a base. Catalytic enhancement depends on the combination of the amine, the base strength, the solvent, steric factors, ion pairing and H‐bonding. A linear relationship between the base strength and the reaction yield has been demonstrated with IL catalysts in the synthesis of formamides and quinazoline‐2,4‐diones. The role of organocatalysts in the reactions indicates that all bases of sufficient strength should be able to catalyze the reactions. However, a physical limit to the extent of a purely base catalyzed reaction mechanism should exist, which needs to be identified, understood and overcome by synergistic or alternative methods.

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“…Since a number of advances and developments in the direct thioesterification of aldehydes have occurred from 1976 to present, a comprehensive review on this interesting research topic seems to be timely. In connection with our review articles on the formation of C-S bonds [11][12][13][14][15][16][17][18][19][20][21][22] and new methodologies in organic synthesis [23][24][25][26][27][28][29][30][31][32][33][34][35], in this Focus-Review, we will highlight recent progress on direct thioesterification of aldehydes with various thiol sources ( Figure 1), with special attention on the mechanistic aspects of the reactions. The cross-dehydrogenative coupling reactions of aldehydes with thiols are discussed first.…”

Section: Introductionmentioning

confidence: 99%

Methods for the direct synthesis of thioesters from aldehydes: a focus review

Jabarullah

Jermsittiparsert

Melnikov

et al. 2019

Journal of Sulfur Chemistry

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Direct C-H bond functionalization chemistry allows the pot-, atom-, and step-economical and original construction of carbon-carbon and carbon-heteroatom bonds starting from hydrocarbons (or hydrocarbon fragments) without requiring pre-functionalization of the starting materials. In this context, synthesis of biologically and synthetically important thioesters through direct thioesterification of aldehydes has recently attracted considerable attention from organic synthetic communities, because aldehydes are cheap and widely abundant chemical materials. This review highlights up-todate developments and accomplishments in this interesting research arena with special emphasis on the mechanistic aspects of the reactions.

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Three-component reaction of amines, epoxides, and carbon dioxide: A straightforward route to organic carbamates

Cited by 53 publications

References 52 publications

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Pivotal Role of the Basic Character of Organic and Salt Catalysts in C−N Bond Forming Reactions of Amines with CO₂

Methods for the direct synthesis of thioesters from aldehydes: a focus review

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Three-component reaction of amines, epoxides, and carbon dioxide: A straightforward route to organic carbamates

Cited by 53 publications

References 52 publications

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Pivotal Role of the Basic Character of Organic and Salt Catalysts in C−N Bond Forming Reactions of Amines with CO2

Methods for the direct synthesis of thioesters from aldehydes: a focus review

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Pivotal Role of the Basic Character of Organic and Salt Catalysts in C−N Bond Forming Reactions of Amines with CO₂