Sc(OTf)<sub>3</sub>‑Catalyzed DiastereoselectiveHydroxyheteroarylation of C–C σ‑Bonds of Bicyclo[1.1.0]butaneswith Azaheterocyclic <i>N</i>‑Oxides

A mild and atom-economical reaction for the Sc(OTf)<sub>3</sub>-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl <i>N</i>-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy for the highly regio- and diastereoselective preparation of azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives and offers a broad substrate scope and high yields.

Publication Details

Journal
Figshare
Published
2025-03-22
DOI
https://doi.org/10.1021/acs.orglett.5c00802.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Sc(OTf)3‑Catalyzed DiastereoselectiveHydroxyheteroarylation of C–C σ‑Bonds of Bicyclo[1.1.0]butaneswith Azaheterocyclic N‑Oxides

Figshare
Catalytic C–H Functionalization Methods
article

Sc(OTf)3‑Catalyzed DiastereoselectiveHydroxyheteroarylation of C–C σ‑Bonds of Bicyclo[1.1.0]butaneswith Azaheterocyclic N‑Oxides

article en

Abstract

A mild and atom-economical reaction for the Sc(OTf)<sub>3</sub>-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl <i>N</i>-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy for the highly regio- and diastereoselective preparation of azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives and offers a broad substrate scope and high yields.

Figshare
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Catalytic C–H Functionalization Methods
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Sc(OTf)<sub>3</sub>‑Catalyzed DiastereoselectiveHydroxyheteroarylation of C–C σ‑Bonds of Bicyclo[1.1.0]butaneswith Azaheterocyclic <i>N</i>‑Oxides · Figshare (2025) | TGRS Research Map | TGRS