Nitrate Reduction for Deaminative Suzuki–Miyaura Coupling of Anilines
We present a deaminative Suzuki-Miyaura-type coupling (SMC) of anilines with nitrate as a diazotization reagent, which integrates transition-metal catalysis with nitrate-based diazonium chemistry for the first time. The synergistic reduction of nitrate by bisulfite and boronic acids allows for both oxidative diazotization with low-valent transition metal redox transformations simultaneously. The reaction utilizes low-hazard, readily available starting materials and reagents. In comparison to previous diazonium-based Suzuki-Miyaura-couplings, the in situ oxidation of anilines by reduction of nitrate allows larger functional group tolerance.
Authors
- Tobias Ritter (ORCID: https://orcid.org/0000-0002-6957-450X)
- Áron Adorján (ORCID: https://orcid.org/0009-0002-4936-4529)
- Manolis Sofiadis (ORCID: https://orcid.org/0000-0002-9419-6520)
- Javier Mateos (ORCID: https://orcid.org/0000-0002-2358-9183)
- Mike Rippegarten
- Chenchen Li (ORCID: https://orcid.org/0000-0002-3251-5450)
- Tim Schulte (ORCID: https://orcid.org/0009-0003-3976-1907)
Institutions
- Max-Planck-Institut für Kohlenforschung (DE)
- RWTH Aachen University (DE)
- FH Aachen (DE)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-05-02
- DOI
- https://doi.org/10.1002/anie.202504012
- Citations
- 7
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 6.55
Funders
- European Commission
- Horizon 2020 Framework Programme