Direct Synthesis of C4-Acyl Indoles via C-H Acylation
Bo-Sheng Zhang1,2, Ze-Qiang Zhang1, Tian-Jiao Guo1
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070, China.
Abstract:
The direct synthesis of C4-acyl indoles deprived of C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C-H acylation for the construction of C4-acyl indoles via a Catellani-Lautens cyclization strategy. In addition, we systematically studied the ortho C-H acylation mechanism of iodoaniline through density functional theory (DFT) calculations and combined experimental results to elucidate the principle of high chemoselectivity brought by triazine benzoate as an acylation reagent.
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