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author：

Li, J. (Li, J..) [1] | Ou, Y. (Ou, Y..) [2] | Zhang, X. (Zhang, X..) [3] | Li, X. (Li, X..) [4] | Liu, X. (Liu, X..) [5] | Liu, C. (Liu, C..) [6] | Chen, F. (Chen, F..) [7]

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Scopus

Abstract：

Benzoyl　groups　are　commonly　found　in　the　structures　of　various　pharmaceuticals,　including　non-steroidal　anti-inflammatory　drugs　(NSAIDs),　central　nervous　system　stimulants,　antihyperlipidemic　agents,　and　hypnotics.　Bicyclo[1.1.1]pentane-ketone　group　can　serve　as　bioisostere　for　benzoyl　groups,　enhancing　3D　spatial　complexity,　reducing　off-target　effects,　and　improving　lipophilicity　and　solubility　of　the　drug　molecules.　Herein,　we　present　a　visible　light-induced　approach　for　the　synthesis　of　bicyclo[1.1.1]pentane-ketone,　characterized　by　mild　reaction　temperature　and　excellent　tolerance　to　oxidation-sensitive　substituents　such　as　-NH2,　-methylthio　and　ferrocenyl　group.　The　method　delivers　all　products　in　moderate　to　high　yields.　Mechanistic　studies　revealed　the　formation　of　tButyl-bicyclo[1.1.1]　pentane　ether　explained　the　requirement　for　stoichiometric　amounts　of　tBuOOH　rather　than　catalytic　quantities,　in　despite　of　the　redox-neutral　nature　of　this　reaction.　©　2025　Fudan　University

Keyword：

Acyl bicyclo[1.1.1]pentane Acyl radical Bioisostere of benzoyl group Propellane Visible light photocatalysis

Community：

  • [ 1 ] [Li J.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 2 ] [Li J.]Qingyuan Innovation Laboratory, Quanzhou, 362801, China
  • [ 3 ] [Li J.]Key Laboratory of Molecule Synthesis and Function Discovery (FujianProvince University), Fuzhou University, Fuzhou, China
  • [ 4 ] [Ou Y.]College of Chemical Engineering, Fuzhou University, Fuzhou, 350108, China
  • [ 5 ] [Zhang X.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 6 ] [Zhang X.]Qingyuan Innovation Laboratory, Quanzhou, 362801, China
  • [ 7 ] [Zhang X.]Key Laboratory of Molecule Synthesis and Function Discovery (FujianProvince University), Fuzhou University, Fuzhou, China
  • [ 8 ] [Li X.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 9 ] [Liu X.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 10 ] [Liu X.]Qingyuan Innovation Laboratory, Quanzhou, 362801, China
  • [ 11 ] [Liu X.]Key Laboratory of Molecule Synthesis and Function Discovery (FujianProvince University), Fuzhou University, Fuzhou, China
  • [ 12 ] [Liu C.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 13 ] [Liu C.]Qingyuan Innovation Laboratory, Quanzhou, 362801, China
  • [ 14 ] [Liu C.]Key Laboratory of Molecule Synthesis and Function Discovery (FujianProvince University), Fuzhou University, Fuzhou, China
  • [ 15 ] [Chen F.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
  • [ 16 ] [Chen F.]Qingyuan Innovation Laboratory, Quanzhou, 362801, China
  • [ 17 ] [Chen F.]China Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, China

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Source ：

Green Synthesis and Catalysis

ISSN： 2666-5549

Year： 2025

8 . 3 0 0

JCR@2023

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ESI Highly Cited Papers on the List： 0 Unfold All

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30 Days PV： 1

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