Cross-Dehydrogenative Coupling of Azoles with α-C(sp3)–H of Ethers and Thioethers under Metal-Free Conditions: Functionalization of H–N Azoles via C–H Activation
The Journal of Organic Chemistry2015Vol. 80(3), pp. 1929–1936
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Hariprasad Aruri, Umed Singh, Sumit Sharma, Satish Gudup, Mukesh Bhogal, Sanjay Kumar, Deepika Singh, Vivek K. Gupta, Rajni Kant, Ram A. Vishwakarma, Parvinder Pal Singh
Abstract
A metal-free cross-dehydrogenative coupling method for the synthesis of N-substituted azoles has been developed. The TBAI/TBHP system catalyzed the coupling of azoles with ethers and thioethers via α-C(sp(3))-H activation. Under the optimized conditions, a diverse range of un/substituted azoles such as 1H-benzimidazole, 9H-purine, 1H-benzotriazole, 1H-1,2,3-triazole, 1H-1,2,4-triazole, and 1H-pyrazole were successfully employed for coupling with various ethers and thioethers such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethyl ether, tetrahydrothiophene, and 1,3-dithiolane.
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