Li Chen-Chen, Adorján Áron, Sofiadis Manolis, Schulte Tim, Mateos Javier, Rippegarten Mike, Ritter Tobias
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470, Mülheim an der Ruhr, Germany.
Institute of Organic Chemistry, WTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Angew Chem Int Ed Engl. 2025 Jul;64(27):e202504012. doi: 10.1002/anie.202504012. Epub 2025 May 28.
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.
我们展示了一种以硝酸盐为重氮化试剂的苯胺脱氨基铃木-宫浦型偶联反应（SMC），该反应首次将过渡金属催化与基于硝酸盐的重氮化学相结合。亚硫酸氢盐和硼酸对硝酸盐的协同还原作用使得低价过渡金属氧化还原转化与氧化重氮化反应能够同时进行。该反应使用的起始原料和试剂危险性低且易于获得。与之前基于重氮盐的铃木-宫浦偶联反应相比，通过硝酸盐还原原位氧化苯胺可实现更大的官能团耐受性。
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