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Peer-reviewedCC BYJournal of the American Chemical Society

Photocatalytic Denitrative Homo- and Cross-Coupling of Nitroalkanes toward the Synthesis of Alkenes

  • Max Dietel1
  • Mangish Ghosh1
  • Hendrik Paps1
  • Zen Shimizu1
  • Jonas Scholl1
  • Michael Andreas Gruber2
  • Oliver Reiser1
  1. 1Universität Regensburg , , ,
  2. 2Universitätsklinikum Regensburg , , ,
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Abstract

Alkenes serve as fundamental motifs across natural products and synthetic molecules, yet efficient, mild, and versatile olefination strategies remain in demand. Nitroalkanes, renowned for their broad reactivity as nucleophiles or corresponding radicals, still offer untapped potential in photocatalysis. Here, we report a unified, photocatalyzed generation of α-nitroalkyl radicals via oxidation of simple, nonprefunctionalized nitronates, followed by addition to another nitronate (formal homo- or cross-coupling) and subsequent double denitration to furnish alkenes. This transformation leverages both the pro-nucleophilic and pro-electrophilic nature of nitroalkanes, challenging the classic McMurry-type coupling protocol. Moreover, the synthetic manifold is scalable and demonstrates its applicability by synthesizing medicinally relevant Combretastatin and lignan-type cores.

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Cite

BibTeXRIS
BibTeX
@article{dietel2026photocatalytic,
  title = {{Photocatalytic Denitrative Homo- and Cross-Coupling of Nitroalkanes toward the Synthesis of Alkenes}},
  author = {Max Dietel and Mangish Ghosh and Hendrik Paps and Zen Shimizu and Jonas Scholl and Michael Andreas Gruber and Oliver Reiser},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = jul,
  doi = {10.1021/jacs.6c06459},
  url = {https://doi.org/10.1021/jacs.6c06459},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Photocatalytic Denitrative Homo- and Cross-Coupling of Nitroalkanes toward the Synthesis of Alkenes
AU  - Max Dietel
AU  - Mangish Ghosh
AU  - Hendrik Paps
AU  - Zen Shimizu
AU  - Jonas Scholl
AU  - Michael Andreas Gruber
AU  - Oliver Reiser
PY  - 2026
DA  - 2026/07/16
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c06459
UR  - https://doi.org/10.1021/jacs.6c06459
AB  - Alkenes serve as fundamental motifs across natural products and synthetic molecules, yet efficient, mild, and versatile olefination strategies remain in demand. Nitroalkanes, renowned for their broad reactivity as nucleophiles or corresponding radicals, still offer untapped potential in photocatalysis. Here, we report a unified, photocatalyzed generation of α-nitroalkyl radicals via oxidation of simple, nonprefunctionalized nitronates, followed by addition to another nitronate (formal homo- or cross-coupling) and subsequent double denitration to furnish alkenes. This transformation leverages both the pro-nucleophilic and pro-electrophilic nature of nitroalkanes, challenging the classic McMurry-type coupling protocol. Moreover, the synthetic manifold is scalable and demonstrates its applicability by synthesizing medicinally relevant Combretastatin and lignan-type cores.
SN  - 0002-7863
SN  - 1520-5126
SN  - 1943-2984
ER  -