Azetidines with All-Carbon Quaternary Centers: Merging Relay Catalysis with Strain Release Functionalization

Che-Ming Hsu, Heng-Bo Lin, Xin-Zhi Hou, Radyn Vanessa Phaz P. Tapales, Chen-Kuei Shih, Shinje Miñoza, Yu-Syuan Tsai, Zong-Nan Tsai, Cheng-Lin Chan and Hsuan-Hung Liao*

*Department of Chemistry, National Sun Yat-sen University, Kaohsiung 80424, Taiwan (R.O.C.), Email: hsuan-hung.liaomail.nsysu.edu.tw

C.-M. Hsu, H.-B. Lin, X.-Z. Hou, R. V. P. P. Tapales, C.-K. Shih, S. Miñoza, Y.-S. Tsai, Z.-N. Tsai, C.-L. Chan, H.-H. Liao, J. Am. Chem. Soc., 2023, 145, 19049-19059.

DOI: 10.1021/jacs.3c06710

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Abstract

A well-orchestrated polar-radical relay strategy based on ring strain release of bench-stable benzoylated 1-azabicyclo[1.1.0]butane enables a nickel-catalyzed Suzuki Csp²-Csp³ cross-coupling with commercially available boronic acids in broad scope to provide all-carbon quaternary-center-bearing azetidines with excellent functional group tolerance, and gram-scale utility.

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proposed mechanism

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Key Words

Azetidines

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ID: J48-Y2023