Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 37, Issue 5, Pages 1117-1126Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc201702020
Keywords
tansition-metal-catalysis; diazo compound; arene; C-H bond functionalization; site selective
Categories
Funding
- Shanghai Pujiang Program [14PJ1403100]
- National Basic Research Program of China [2015CB856600]
- National Natural Science Foundation of China [21372084, 21425205, 21572065]
- Changjiang Scholars and Innovative Research Team in University
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C-H bond functionalization has been one of the most important subject in chemistry. How to control the site selectivity of C-H bond is the key issue and remain challenge. Transition-metal-catalyzed organic tranformation of diazo compounds, such as X-H (X=O, N, S, etc.) insertion, cyclopropanation, cross-coupling reactions and C(sp(3))-H functionalization, have been well established, whereas the C(sp(2))-H functionalization using diazo compounds is less developed. This review will summarize the progress in transition-metal-catalyzed C(sp(2))-H functionalization of arenes with diazo compounds. To realize the site selectivity, two strategies are utilized. One is directed C-H activation, which gives the ortho-selective CH functionalization products. The other is undirected approach, which normally exhibits para-selectivity. In order to understand these reactions, the mechanisms for selected examples are also provided.
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