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      Cycloamination strategies for renewable N-heterocycles

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          Abstract

          Efficient amination strategies for synthesis of N-heterocycles from functional molecules (bottom-up) or from biomass (top-down) via sustainable C–N/C–X bond chemistry.

          Abstract

          Biomass resources have infinite possibilities for introducing nitrogen, sulfur, or phosphorus heteroatoms into their structures by virtue of controllable carbon–heteroatom bond formation. In this review, cycloamination approaches for thermal (catalyst-free) and catalytic transformation of biomass feedstocks into N-heterocyclic molecules including mechanistic pathways are analyzed. Bottom-up (small molecule substrates) and top-down (large molecule substrates) are considered. Sustainable routes for synthesis of five-membered (pyrroles, pyrrolidones, pyrazoles, imidazoles), six-membered (pyridines, pyrazines), fused (indoles, benzimidazoles), and other relevant azaheterocycles are critically assessed. Production of biomass-derived six-, seven-, and eight-membered as well as fused N-heterocyclic compounds with present approaches have relatively low selectivities. Attention to methods for forming analogous sulfur or phosphorus heteroatom compounds from biomass resources using either bottom-up or top-down strategies appear to have been greatly overlooked. Synthetic auxiliaries (heating modes, nitrogen sources) that enhance reaction efficiency and tunability of N-heterocyclic ring size/type are considered and plausible reaction mechanisms for pivotal pathways are developed.

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          Transformation of carbon dioxide.

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            N-heterocyclic carbenes in late transition metal catalysis.

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              Using carbon dioxide as a building block in organic synthesis.

              Carbon dioxide exits in the atmosphere and is produced by the combustion of fossil fuels, the fermentation of sugars and the respiration of all living organisms. An active goal in organic synthesis is to take this carbon--trapped in a waste product--and re-use it to build useful chemicals. Recent advances in organometallic chemistry and catalysis provide effective means for the chemical transformation of CO₂ and its incorporation into synthetic organic molecules under mild conditions. Such a use of carbon dioxide as a renewable one-carbon (C1) building block in organic synthesis could contribute to a more sustainable use of resources.
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                Author and article information

                Contributors
                Journal
                GRCHFJ
                Green Chemistry
                Green Chem.
                Royal Society of Chemistry (RSC)
                1463-9262
                1463-9270
                February 10 2020
                2020
                : 22
                : 3
                : 582-611
                Affiliations
                [1 ]Biomass Group
                [2 ]College of Engineering
                [3 ]Nanjing Agricultural University
                [4 ]Nanjing
                [5 ]China
                [6 ]Graduate School of Environmental Studies
                [7 ]Tohoku University
                [8 ]Sendai
                [9 ]Japan
                [10 ]Department of Chemical Engineering
                [11 ]Faculty of Engineering
                [12 ]Fukuoka University
                [13 ]Fukuoka 814-0180
                Article
                10.1039/C9GC03655E
                © 2020
                Product
                Self URI (article page): http://xlink.rsc.org/?DOI=C9GC03655E

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