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February 5, 2026Organic Letters0 citations

Regioselective 1,2-Diamination of Aryl-Substituted 1,3-Dienes via Axial PPh 3 -Coordinated Dirhodium(II) Catalysis

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LZLi ZhangCWChuanyong WangXRXinli Rong

Key Points

  • The aim is to develop a regioselective method for 1,2-diamination using dirhodium catalysis and axial PPh3 coordination.
  • Utilized axial PPh3 coordination in dirhodium catalysis
  • Employed N-fluorobenzenesulfonimide as oxidant and nitrogen source
  • Conducted reactions with various functional groups and evaluated yields
  • Achieved up to 91% yield in 1,2-diamination reactions
  • Demonstrated broad functional group tolerance with 35 examples
  • Highlighted gram-scale scalability of the method

Abstract

Axial PPh3 coordination enables the regioselective 1,2-diamination of aryl-substituted 1,3-dienes using dirhodium catalysis, employing N-fluorobenzenesulfonimide as the oxidant and nitrogen source. This base-free protocol proceeds via a PPh3-stabilized dirhodium(II,III) species, facilitating efficient nitrogen radical transfer via the trans effect. The method features broad functional group tolerance (35 examples, up to 91% yield) and gram-scale scalability. This work highlights the potential of axial electronic tuning as a general strategy for controlling reactivity in a dirhodium-catalyzed radical reaction.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/698434c0f1d9ada3c1fb33bfhttps://doi.org/10.1021/acs.orglett.5c05444
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