首页|Chemo-and Regioselective Multiple C(sp2)—H Insertions of Malonate Metal Carbenes for Late-Stage Functionalizations of Azahelicenes
Chemo-and Regioselective Multiple C(sp2)—H Insertions of Malonate Metal Carbenes for Late-Stage Functionalizations of Azahelicenes
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NSTL
Chiral quinacridines react up to four times, step-by-step, with a-diazomalonates under Ru~(II) and Rh~(II) catalysis. By selecting the catalyst, [CpRu(CH3CN)3][PF6] (Cp = cyclopentadienyl) or Rh2-(oct)4, chemo and regioselective insertions of derived metal carbenes are achieved in favor of mono-or bis-functionalized malonate derivatives, respectively, (r.r. > 49:1, up to 77% yield, 12 examples). This multi-introduction of malonate groups is particularly useful to tune optical and chemical properties such as absorption, emission or Br0nsted acidity but also cellular bioimag-ing. Density-functional theory further elucidates the origin of the carbene insertion selectivity and also showcases the importance of conformations in the optical response.
NSTL
