Donor-Stabilized Silacyclobutanone: A Precursor of 1‑Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature

The
synthesis of donor-stabilized silacyclobutanone 2 was
successfully realized by the reaction of silacyclopropylidene 1 with benzaldehyde in the presence of a Lewis acid catalyst.
Of particular interest, silacyclobutanone 2 evolves at
room temperature via a retro-[2 + 2]-cycloaddition reaction, leading
to an original NHC-stabilized 1-silaketene 4 and cis-stilbene.

本研究通过硅杂环亚丙基1与苯甲醛在路易斯酸催化剂存在下的反应，成功实现了给体稳定的硅杂环丁酮2的合成。尤为值得关注的是，硅杂环丁酮2可在室温下经逆[2+2]环加成反应分解，生成首例氮杂环卡宾（NHC）稳定的1-硅烯酮4与顺式二苯乙烯。