Synthesis and Photocatalytic Three-Component Ring-Opening of 3‑Substituted-1-azabicyclo[1.1.0]butanes toward 3,3-Disubstituted N‑Sulfonylazetidines.
- 1Department of Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, Mainz 55128, Germany.
- 2Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos 13565-905, Brazil.
Abstract
Aryl-substituted azetidines are found in pharmacologically active compounds; however, efficient synthetic methods to access this scaffold remain limited. Existing approaches predominantly enable the synthesis of azetidines bearing electron-rich aryl substituents. Herein, we report a new and straightforward route to 3-substituted 1-azabicyclo[1.1.0]-butanes (ABBs) from commercially available tert-butyl 3-oxoazetidine-1-carboxylate in four steps. The ABBs were then applied in a three-component photocatalytic ring-opening reaction, affording 3,3-diaryl-N-sulfonylazetidines with a variety of electron-poor (hetero)-arene units, a previously inaccessible chemical space. Under the optimized conditions, 29 examples of 3,3-diaryl-N-sulfonylazetidines were prepared in yields of up to 72%.
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BibTeX
@article{furniel2026synthesis,
title = {{Synthesis and Photocatalytic Three-Component Ring-Opening of 3‑Substituted-1-azabicyclo[1.1.0]butanes toward 3,3-Disubstituted N‑Sulfonylazetidines.}},
author = {Lucas G Furniel and Niklas Ehlenz and Dieter Schollmeyer and Arlene G Corrêa and Till Opatz},
journal = {JACS Au},
year = {2026},
month = sep,
doi = {10.1021/jacsau.6c01100},
url = {https://europepmc.org/article/MED/42953189},
note = {CC BY},
}
RIS
TY - JOUR
TI - Synthesis and Photocatalytic Three-Component Ring-Opening of 3‑Substituted-1-azabicyclo[1.1.0]butanes toward 3,3-Disubstituted N‑Sulfonylazetidines.
AU - Lucas G Furniel
AU - Niklas Ehlenz
AU - Dieter Schollmeyer
AU - Arlene G Corrêa
AU - Till Opatz
PY - 2026
DA - 2026/09/07
JO - JACS Au
DO - 10.1021/jacsau.6c01100
UR - https://europepmc.org/article/MED/42953189
AB - Aryl-substituted azetidines are found in pharmacologically active compounds; however, efficient synthetic methods to access this scaffold remain limited. Existing approaches predominantly enable the synthesis of azetidines bearing electron-rich aryl substituents. Herein, we report a new and straightforward route to 3-substituted 1-azabicyclo[1.1.0]-butanes (ABBs) from commercially available tert-butyl 3-oxoazetidine-1-carboxylate in four steps. The ABBs were then applied in a three-component photocatalytic ring-opening reaction, affording 3,3-diaryl-N-sulfonylazetidines with a variety of electron-poor (hetero)-arene units, a previously inaccessible chemical space. Under the optimized conditions, 29 examples of 3,3-diaryl-N-sulfonylazetidines were prepared in yields of up to 72%.
SN - 2691-3704
ER -