A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane
- 1College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Zhejiang Key Laboratory of Organosilicon Material Technology, Hangzhou Normal University, Hangzhou 311121, China
- 2Department of Chemistry, Zhejiang University, Hangzhou 310027, China
Abstract
Bicyclo[1.1.1]pentanes (BCPs) constitute prominent bioisosteric replacements for aromatic frameworks and are frequently incorporated into diverse pharmaceutical compounds. However, current synthetic routes, especially those for the synthesis of sulfonyl BCP derivatives, are hampered by narrow substrate scope and limited functional group tolerance. These constraints underscore the demand for more versatile and operationally practical synthetic strategies. Here, we disclose a general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane, enabling the modular synthesis of multifunctional sulfonyl BCPs. This platform facilitates the construction of diverse sulfonyl-BCP derivatives, including ─Cl, ─Br, ─I, ─CN, ─SCD 3 , ─H, ─HetAr, ─COAr, ─SAr, ─N═NAr, etc., with exceptional functional group tolerance and scalability. The utility of this approach is further enhanced by its applicability to late-stage functionalization of pharmacologically active compounds and derivative synthesis. Mechanistic investigations and DFT calculation revealed that this work involves the ligand-accelerated manganese-catalyzed halogen-atom transfer (XAT) radical addition process.
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BibTeX
@article{xu2026general,
title = {{A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane}},
author = {Jun Xu and Lin Li and Qing Pang and M Chen and Huamin Wang and Pengfei Zhang},
journal = {Science Advances},
year = {2026},
month = jun,
doi = {10.1126/sciadv.aeg5293},
url = {https://doi.org/10.1126/sciadv.aeg5293},
note = {CC BY},
}
RIS
TY - JOUR
TI - A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane
AU - Jun Xu
AU - Lin Li
AU - Qing Pang
AU - M Chen
AU - Huamin Wang
AU - Pengfei Zhang
PY - 2026
DA - 2026/06/26
JO - Science Advances
DO - 10.1126/sciadv.aeg5293
UR - https://doi.org/10.1126/sciadv.aeg5293
AB - Bicyclo[1.1.1]pentanes (BCPs) constitute prominent bioisosteric replacements for aromatic frameworks and are frequently incorporated into diverse pharmaceutical compounds. However, current synthetic routes, especially those for the synthesis of sulfonyl BCP derivatives, are hampered by narrow substrate scope and limited functional group tolerance. These constraints underscore the demand for more versatile and operationally practical synthetic strategies. Here, we disclose a general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane, enabling the modular synthesis of multifunctional sulfonyl BCPs. This platform facilitates the construction of diverse sulfonyl-BCP derivatives, including ─Cl, ─Br, ─I, ─CN, ─SCD 3 , ─H, ─HetAr, ─COAr, ─SAr, ─N═NAr, etc., with exceptional functional group tolerance and scalability. The utility of this approach is further enhanced by its applicability to late-stage functionalization of pharmacologically active compounds and derivative synthesis. Mechanistic investigations and DFT calculation revealed that this work involves the ligand-accelerated manganese-catalyzed halogen-atom transfer (XAT) radical addition process.
SN - 2375-2548
ER -