Zhang Yunxiao, Zhang Yizhi, Ye Chen, Qi Xiaotian, Wu Li-Zhu, Shen Xiao
The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, Wuhan, China.
Shenzhen Research Institute of Wuhan University, Wuhan University, Shenzhen, China.
Nat Commun. 2022 Oct 16;13(1):6111. doi: 10.1038/s41467-022-33730-x.
Developing photo-induced cascade cyclization of alkene-tethered acylsilanes is challenging, because acylsilanes are unstable under light irradiation. Herein, we report that the energy transfer from excited acylsilanes to a photocatalyst that possesses lower triplet energy can inhibit the undesired decomposition of acylsilanes. With neutral Eosin Y as the photocatalyst, an efficient synthesis of cyclopentanol derivatives is achieved with alkene-tethered acylsilanes and allylic sulfones. The reaction shows broad substrate scope and the synthetic potential of this transformation is highlighted by the construction of cyclopentanol derivatives which contain fused-ring or bridged-ring.
开发烯烃连接的酰基硅烷的光致级联环化反应具有挑战性，因为酰基硅烷在光照下不稳定。在此，我们报道从激发态的酰基硅烷到具有较低三重态能量的光催化剂的能量转移可以抑制酰基硅烷的不期望的分解。以中性曙红Y作为光催化剂，通过烯烃连接的酰基硅烷和烯丙基砜实现了环戊醇衍生物的高效合成。该反应具有广泛的底物范围，并且通过构建含有稠环或桥环的环戊醇衍生物突出了这种转化的合成潜力。
