
As a convenient and environmentally friendly organic synthesis route, selective C-H bond functionalization reactions attract more and more attention, and have a great potential to find wide applications in pharmaceutical chemistry, natural products, syntheses and preparation of organic functional materials. On the other hand, the decarboxylative cross-coupling that uses arene carboxylic acids as equivalent of expensive organometallic reagents for carbon-carbon or carbon-heteroatom bond formation has become extremely attractive synthetic approach largely due to ready availability and easy-to-handle properties of this class of compounds.
The research group headed by Prof. SU Weiping at the State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter (FJIRSM) has made progress on the development of transition-metal catalyzed C-H bond functionalization and decarboxyative cross-coupling reactions:
1) realizing the direct C-H bond arylation of thiophene and polyfluoroarenes using arene carboxylic acids as arylating reagent, which show good functional group compatibility, and provide an atom-economical and efficient route for biaryl synthesis (Angew. Chem. Int. Ed. 2011, 50, 9926 –9930; J. Org. Chem. 2011, 76, 882).
2) achieving a selective formylation and acylation of free (N-H) indoles under mild condition, which overcomes the drawback of harsh conditions in traditional formylation and acylation reactions, and will find application in modifications of complexity compound owing to its good functional group compatibility (J. Am. Chem. Soc., 2011, 133, 11924; Chem. Comm., 2011, 9660).
3) in cooperation with Peking University, establishing the first example of the construction of substituted benzene rings by palladium-catalyzed direct cross-coupling of olefins, which paved a new way to synthesis of substituted benzene rings, hopefully overcome the limitation resulted from orientation effect of substituents on benzene rings in traditional preparation of polysubstituted benzene rings (Angew. Chem. Int. Ed., 2011, 50, 9926).
At the same time, Prof. SU’s group also reported the first example of direct alkynylation of C-H bond using 1,10-phenanthroline-Cu complex as catalyst and O2 as an oxidant, this new discovery offer an effective approach to organic photoelectric functional materials (J. Am. Chem. Soc., 2010, 132, 2522).
Furthermore, using palldadium complex as catalyst and copper complex as oxidant, they realized the oxidative C−H/C−H cross-coupling of electron-deficient polyfluoroarenes with simple arenes, of which the selectivity stems from the difference in electronic property between two substrates (J. Am. Chem. Soc., 2010, 132, 16377).

Figure 1: Palladium-catalyzed decarboxylative C-H bond arylation of thiophenes (Image by SU Weiping)

Figure 2: Construction of substituted benzene rings by direct cross-coupling of olefins (Image by SU Weiping)
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