Markl Christian, Kar Sourav, Lubczyk Lukas, Hammond Kai, Dewhurst Rian D, Braunschweig Holger
Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany
Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany.
Chem Sci. 2025 Sep 16. doi: 10.1039/d5sc04751j.
Boron-containing fused heterocycles have received considerable attention due to their unique structures, bonding, and intriguing properties. However, progress in this area has been hampered by a lack of efficient synthetic methodologies. In this study, we demonstrate the reactivity of a diboracumulene, LBBL (L = cyclic (alkyl)(amino)carbene, CAAC), with various nitrogen-containing heterocyclic thiols. These straightforward reactions result in the partial or complete cleavage of the B-B multiple bonds in the diboracumulene, along with S-H bond activation in the thiol units, leading to the formation of a range of tricyclic and tetracyclic B,N,S-heterocycles. Notably, the tricyclic B,N,S-heterocycle exhibits π aromaticity in all three of its rings.
含硼稠合杂环因其独特的结构、键合和有趣的性质而受到了广泛关注。然而，该领域的进展因缺乏高效的合成方法而受到阻碍。在本研究中，我们展示了二硼累积烯LBBL（L = 环状（烷基）（氨基）卡宾，CAAC）与各种含氮杂环硫醇的反应活性。这些直接的反应导致二硼累积烯中的B-B多重键部分或完全断裂，同时硫醇单元中的S-H键被活化，从而形成一系列三环和四环B，N，S-杂环。值得注意的是，三环B，N，S-杂环在其所有三个环中均表现出π芳香性。
