Recently, researchers from the State Key Laboratory of Carbonylation and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences have made new progress in the direct functionalization of CH bonds in nitrogen-containing heterocyclic compounds. Under the catalysis of transition metals, the linear carbonylation and phosphorylation of nitrogen-containing heterocyclic compounds of indole and oxazine are efficiently and highly selective. The resulting functionalized heterocyclic compounds are important organic intermediates.

The researchers developed a new class of rhodium-catalyzed direct carbonylation of the indole 3-position CH bond to synthesize indole-3-carboxylic acid esters. This system is not only efficient and Directly carbonylate the CH bond on the N-substituted indole-3-position with high selectivity, and can also highly selectively carbonylate the CH bond on the indole-3-position with no substituent at the N-position. Catalyzed oxidative carbonylation reactions usually take place at the more active NH site and are very different. The research results were published in Chem. Comm. (2011, 47, 12553-12555).

Subsequently, the researchers reported the first direct phosphorylation reaction of Pd (OAc) 2 as a metal catalyst, bipyridine or proline as a ligand, and phosphite and oxazane. In the absence of alkali, through the activation of PH and CH, the oxidative coupling synthesis of 2-oxaphosphite was achieved with high selectivity, and the mechanism of this new type of CP bond formation reaction was studied. This method opens up a new way to synthesize corresponding arylphosphine-containing compounds by directly constructing CP bonds. The research results were published in Chem. Comm. (2012, 48, 5181-5183).

The above research work was supported by the "Hundred Talents Program" of the Chinese Academy of Sciences and the National Natural Science Foundation of China (21002106, 21133011).

Rhodium-catalyzed direct carbonylation of the 3-position CH bond of indole to synthesize indole-3-carboxylate

Palladium-catalyzed direct phosphorylation of oxazane to synthesize 2-oxaphosphite new method

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