Three-Component Reaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes

Herein, we present a three-component reaction through Rh(III)-catalyzed strain release of bicyclo[1.1.0]butanes (BCBs) to synthesize substituted acrylamides. This protocol represents the first example of a nucleophilic attack on the Rh(V) nitrenoid complex generated by the coupling of phenoxyacetamides and strained BCBs. The reaction proceeds under mild conditions and demonstrates broad compatibility with various functional groups on both phenoxyacetamides and nucleophiles, affording valuable substituted acrylamides. Furthermore, the products can be further transformed into important building blocks for synthesis. Preliminary mechanistic studies support the proposed catalytic cycle.本文报道了一种通过铑(III)（Rh(III)）催化双环[1.1.0]丁烷（bicyclo[1.1.0]butanes，BCBs）的张力释放来合成取代丙烯酰胺的三组分反应。该策略首次实现了苯氧乙酰胺与张力型双环[1.1.0]丁烷偶联所生成的铑(V)（Rh(V)）氮宾络合物的亲核进攻。该反应可在温和条件下进行，对苯氧乙酰胺和亲核试剂上的各类官能团均具有良好的兼容性，可得到具有较高应用价值的取代丙烯酰胺产物。此外，所得产物还可进一步转化为重要的有机合成砌块。初步机理研究验证了所提出的催化循环机制。