Journal
GREEN CHEMISTRY
Volume 22, Issue 3, Pages 582-611Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9gc03655e
Keywords
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Funding
- National Natural and Science Foundation of China [21878161]
- Nanjing Agricultural University [68Q-0603]
- International Postdoctoral Exchange Fellowship Program of China [20170026]
- Postdoctoral Science Foundation of China [2016M600422]
- Jiangsu Postdoctoral Research Funding Plan [1601029A]
- Japan Society for the Promotion of Science (JSPS) (Japan) [19K15347]
- Tohoku University Center for Gender Equality Promotion
- Grants-in-Aid for Scientific Research [19K15347] Funding Source: KAKEN
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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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