Electrochemical synthesis of 2-alkyl-4- phenylalkan-2-ols via cathodic reductive coupling of alkynes with unactivated aliphatic ketones Anil Balajirao Dapkekar and Gedu Satyanarayana a Indian Institute of Technology Hyderabad, India Herein, we present an efficient electrochemical method for synthesizing 2-alkyl-4-phenylalkan-2-ols through an electrochemically driven cathodic reductive coupling of the terminal and internal acetylenes with unactivated aliphatic ketones under mild conditions. The process proceeds through a ketyl radical, which then activates the aryl acetylene and causes complete reduction of the triple bond of the acetylene moiety. This strategy is environmentally benign and exhibits a broad substrate scope with ubiquitously available starting materials. Graphical Abstract:
References 1. A. B. Dapkekar and G. Satyanarayana, Chem. Commun. , 2023, 59 , 2915–2918. 2. Hu, B. K. Peters, C. A. Malapit, J. C. Vantourout, P. Wang, J. Li, L. Mele, P.-G. Echeverria, S. D. Minteer and P. S. Baran, J. Am. Chem. Soc., 2020, 142 , 20979–20986. 3. Seo and T. F. Jamison, Org. Lett., 2019, 21 , 10159–10163. 4. Kingston, M. D. Palkowitz, Y. Takahira, J. C. Vantourout, B. K. Peters, Y. Kawamata and P. S. Baran, Acc. Chem. Res., 2020, 53 , 72–83.
P25F
© The Author(s), 2023
Made with FlippingBook Learn more on our blog