Journal
CHEMICAL REVIEWS
Volume 117, Issue 13, Pages 9302-9332Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.7b00021
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Funding
- JST ERATO, Japan [JPMJER1302]
- JSPS KAKENHI [JP26888007]
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [17H04868] Funding Source: KAKEN
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Azines, which are six-membered aromatic compounds containing one or more nitrogen atoms, serve as ubiquitous structural cores of aromatic species with important applications in biological and materials sciences. Among a variety of synthetic approaches toward azines, C-H functionalization represents the most rapid and atom-economical transformation, and it is advantageous for the late-stage functionalization of azine-containing functional molecules. Since azines have several C-H bonds with different reactivities, the development of new reactions that allow for the functionalization of azines in a regioselective fashion has comprised a central issue. This review describes recent advances in the C-H functionalization of azines categorized as follows: (1) SNAr reactions, (2) radical reactions, (3) deprotonation/functionalization, and (4) metal-catalyzed reactions.
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