期刊
CHEMICAL SOCIETY REVIEWS
卷 50, 期 14, 页码 8214-8247出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cs00360g
关键词
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资金
- Engineering and Physical Sciences Research Council [EP/N509711/1, EP/T517811/1]
- European Union [721902]
- AstraZeneca [EP/L015838/1]
- Diamond Light Source [EP/L015838/1]
- Defence Science and Technology Laboratory [EP/L015838/1]
- Evotec [EP/L015838/1]
- GlaxoSmithKline [EP/L015838/1]
- Novartis [EP/L015838/1]
- Syngenta [EP/L015838/1]
- Takeda [EP/L015838/1]
- UCB [EP/L015838/1]
- Vertex [EP/L015838/1]
- Janssen [EP/L015838/1]
- Pfizer [EP/L015838/1]
- Marie Curie Actions (MSCA) [721902] Funding Source: Marie Curie Actions (MSCA)
This review discusses recent advances in difluoromethylation processes, focusing on X-CF2H bond formation and the development of various difluoromethylation reagents. Metal-based methods have shown promise in transferring CF2H to C(sp(2)) sites, while Minisci-type radical chemistry has been successfully applied to difluoromethylate C(sp(2))-H bonds.
This review describes the recent advances made in difluoromethylation processes based on X-CF2H bond formation where X is C(sp), C(sp(2)), C(sp(3)), O, N or S, a field of research that has benefited from the invention of multiple difluoromethylation reagents. The last decade has witnessed an upsurge of metal-based methods that can transfer CF2H to C(sp(2)) sites both in stoichiometric and catalytic mode. Difluoromethylation of C(sp(2))-H bond has also been accomplished through Minisci-type radical chemistry, a strategy best applied to heteroaromatics. Examples of electrophilic, nucleophilic, radical and cross-coupling methods have appeared to construct C(sp(3))-CF2H bonds, but cases of stereoselective difluoromethylation are still limited. In this sub-field, an exciting departure is the precise site-selective installation of CF2H onto large biomolecules such as proteins. The formation of X-CF2H bond where X is oxygen, nitrogen or sulfur is conventionally achieved upon reaction with ClCF2H; more recently, numerous protocols have achieved X-H insertion with novel non-ozone depleting difluorocarbene reagents. All together, these advances have streamlined access to molecules of pharmaceutical relevance, and generated interest for process chemistry.
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