Nickel‐Catalyzed <i>O</i> ‐Alkylisourea‐Enabled Electrochemical Radical C(sp <sup>3</sup> )−C(sp <sup>2</sup> ) Cross‐Coupling
Abstract
Abstract The development of efficient methods to employ naturally abundant alcohol derivatives as C(sp 3 ) precursors for deoxygenative carbon–carbon (C–C) cross‐coupling holds significant value for expanding sp 3 ‐enriched chemical space. While progress has been made in this area, the field lacks readily accessible, bench‐stable alkylation reagents capable of undergoing reductive activation to generate alkyl radicals. Herein, we report an electroreductive nickel‐catalyzed system for efficient C(sp 3 )–C(sp 2 ) radical cross‐coupling between aryl electrophiles (halides, triflates, tosylates, and boronic acids) and O ‐alkylisoureas as radical progenitors. This protocol demonstrates broad substrate scope with good functional group compatibility. Its synthetic utility is highlighted through the preparation of beclobrate analogs and bifonazole, as well as late‐stage functionalization of bioactive compounds. Mechanistic investigations support a radical cross‐coupling pathway for this transformation.
Article Details
Authors (9)
Yonggang Yan
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering
Weikang Xiong
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Institute of New Concept Sensors and Molecular Materials, and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an Shaanxi China
Shasha Li
Zhenhua Wang
Tengfei Kang
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, U.K.
Gang Li
State Key Laboratory of Molecular Reaction Dynamics and Dalian Coherent Light Source Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China
Geyang Song
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering
Jianyang Dong
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering
Dong Xue
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering