期刊
SYNTHESIS-STUTTGART
卷 52, 期 11, 页码 1585-1601出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690844
关键词
iminyl radicals; C-C bond cleavage; cyanoalkylation; nitriles; single-electron transfer
资金
- National Key Basic Research Program For Youth, China [2016YFA0602900]
- National Science Foundation (NSF) of Guangdong Province for Distinguished Young Scholars [2016A030306029]
- National Natural Science Foundation of China (NSFC) [21871300]
- NSFC [21801101]
Abstract Alkyl nitriles are versatile building blocks in organic synthesis because the cyano group can be easily converted into other functional groups. Iminyl-radical-triggered C-C bond cleavage of cycloketone oxime derivatives provides a practical route to access distal cyano-substituted alkyl radicals, which has given chemists a new radical reaction platform for the synthesis of diverse alkyl nitriles. This review provides an overview of various types of radical cyanoalkylation via ring opening of cycloketone oxime derivatives. 1 Introduction 2 C-C Bond Formation 2.1 Alkenes as Radical Acceptors 2.2 Aromatic Rings as Radical Acceptors 2.3 Organometallic Reagents as Radical Acceptors 2.4 Cyanoalkyl-Radical-Triggered Cyclization Reactions 2.5 Miscellaneous 3 C-Heteroatom Bond Formation 3.1 C-O Bond Formation 3.2 C-N Bond Formation 3.3 C-S Bond Formation 3.4 C-Halogen Bond Formation 3.5 C-B Bond Formation 4 Conclusion
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