Designs and Strategies for the Halo‐Functionalization of Diazo Compounds

Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, incl...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3185-3212
Main Authors: Khanal, Hari Datta, Thombal, Raju S., Maezono, Shizuka Mei B., Lee, Yong Rok
Format: Article
Language:English
Subjects:
Chemical compounds
diazo compounds
dihaloolefination
Halides
Halogenation
Organic chemistry
Reagents
trifluoromethylation
trifluoromethylthiolation
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Summary:Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, including halogenation, dihalogenation, dihaloolefination, trifluoromethylation, trifluoromethylthiolation, and trifluoromethoxylation, using diverse halogenating agents. Special emphasis is placed on the challenges and achievements of these halogenation strategies. For selected examples, mechanisms leading to unusual reactivities and selectivities are discussed in detail to show the impressive and unique properties of these halogenation reactions. Furthermore, we hope to encourage the scientific community to explore the benefits of using diazo compounds as a straightforward and step‐economic alternative approach to the construction of carbon‐halogen bonds.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800340