Copper-Mediated DNA-Compatible One-Pot Click Reactions of Alkynes with Aryl Borates and TMS-N3.

Yi Qu, Huanan Wen, Rui Ge, Yanfen Xu, Hong Gao, Xiaodong Shi, Jiangong Wang, Weiren Cui, Wenji Su, Hongfang Yang, Letian Kuai, Alexander L Satz, Xuanjia Peng

Organic letters 2020 Jun 05

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We report a DNA-compatible copper-mediated efficient synthesis of 1,2,3-triazoles via a one-pot reaction of aryl borates with TMS-N3 followed by a click cycloaddition reaction. Employing the binuclear macrocyclic nanocatalyst Cu(II)-β-cyclodextrin, the reactions were performed under mild conditions with high conversions and wide functional group tolerance. We also demonstrate the reaction application toward a one-pot DNA-compatible intramolecular macrocyclization. Our optimized reaction protocol results in no significant DNA damage as judged by qPCR analysis and Sanger sequencing data.

Citation

Yi Qu, Huanan Wen, Rui Ge, Yanfen Xu, Hong Gao, Xiaodong Shi, Jiangong Wang, Weiren Cui, Wenji Su, Hongfang Yang, Letian Kuai, Alexander L Satz, Xuanjia Peng. Copper-Mediated DNA-Compatible One-Pot Click Reactions of Alkynes with Aryl Borates and TMS-N3. Organic letters. 2020 Jun 05;22(11):4146-4150