Ding Ran, Gang Dong, Tang Xu, Wu Tao, Liu Lei, Mao Yue-Yuan, Li Zi-Rong, Gao Hui
College of Chemistry and Materials Engineering, Anhui Science and Technology University, Chuzhou, Anhui 233100, P. R. China.
School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
J Org Chem. 2024 Nov 1;89(21):15733-15738. doi: 10.1021/acs.joc.4c01835. Epub 2024 Oct 16.
Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via the cracking of aryl C-H bonds. In contrast, the radical cascade cyclization of linear dienes through the cracking of vinyl C-H bonds to construct nonbenzene-fused ring frameworks with endocyclic double bonds has significantly lagged behind, and major advances have largely been restricted to the generation of 5-membered heterocycles, such as pyrrolinones. Herein, we report the silver-mediated regioselective sulfonylation-cyclization of linear dienes with sodium sulfinates to form sulfonylated 6- and 7-membered cyclic enamines.
通过芳基C-H键的裂解，在杂芳基或芳基连接的烯烃的自由基级联环化反应中构建稠合苯骨架方面取得了显著进展。相比之下，通过乙烯基C-H键的裂解，线性二烯的自由基级联环化反应以构建具有环内双键的非稠合苯环骨架的研究则明显滞后，并且主要进展在很大程度上仅限于生成五元杂环，如吡咯啉酮。在此，我们报道了银介导的线性二烯与亚磺酸钠的区域选择性磺酰化-环化反应，以形成磺酰化的六元及七元环状烯胺。
