Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, Kolkata-700032, India.
Chem Commun (Camb). 2020 Dec 21;56(100):15659-15662. doi: 10.1039/d0cc06538b. Epub 2020 Dec 8.
An atom-economic Pd(ii)-catalysed cascade cyclisation of 2-(biphenylethynyl)anilines tethered to an aldehyde or cyano group leads to the formation of dibenzo[5,6:7,8]cycloocta[1,2-b]indol-10-ols 6 or dibenzo[5,6:7,8]cycloocta[1,2-b]indol-10(15H)-ones 8 with high yields (up to 95%). The reaction proceeds via amino-palladation of the alkyne followed by nucleophilic addition onto the aldehyde/cyano group. Treatment of 6 with p-TsOH·HO smoothly provided cyclooctatetraene (COT) derivatives 7.
一种原子经济性的 Pd(ii)催化的 2-(联苯乙炔基)苯胺与醛或氰基基团连接的级联环化反应，导致二苯并[5,6:7,8]环辛[1,2-b]吲哚-10-醇 6 或二苯并[5,6:7,8]环辛[1,2-b]吲哚-10(15H)-酮 8 的高产率（高达 95%）的形成。该反应通过炔烃的氨基钯化进行，然后亲核加成到醛/氰基基团上。用对甲苯磺酸·HO 处理 6 可顺利提供环辛四烯（COT）衍生物 7。
