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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
A Unified Photocatalytic Strategy for Fluoroalkylated and Cyanated α-Tertiary Amino/Glycolic Acids via a
Ya-Zhen Zeng1, Rui Zhu1, Chi Zhang1
1Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Anhui Provincial Key Laboratory of Synthetic Chemistry and Applications, and College of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, P. R. China.
Abstract:
A redox-neutral, metal-free, visible-light-driven strategy is developed for constructing fluoroalkylated and cyanated α-tertiary amino acids (ATAAs) via a radical migration-mediated radical-polar cascade. This mild protocol generates multifunctional α-carbonyl carbocations, which are trapped by nitriles to afford diverse ATAAs with a broad scope. The synthetic utility is demonstrated through the late-stage modification of bioactive molecules. Remarkably, trapping the carbocations with H2O provides fluoroalkylated and cyanated α-tertiary glycolic acids (ATGAs) in good yields, thus offering a powerful tool for privileged pharmaceutical scaffold development.
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