PhICl2/KSeCN Mediated Synthesis of Selenopheno[3,2‑b]indoles and 3‑Selenocyanato-2-benzoselenophene Indoles from 1,3-Diynes via Double Electrophilic Cyclization

A hypervalent iodine-enabled double intramolecular electrophilic cyclization of 1,3-diynes has been employed in the synthesis of selenopheno[3,2-b]indoles and 3-selenocyanato-2-benzoselenophene indoles. A plausible mechanism involving the in situ formation of the reactive Cl-SeCN species from the reaction of PhICl2 and KSeCN, followed by cascade cyclization involving C–N/C–Se bond formations, was postulated.

本研究采用基于高价碘(hypervalent iodine)介导的1,3-二炔分子内双亲电环化策略，实现了硒吩并[3,2-b]吲哚与3-硒氰基-2-苯并硒吩吲哚的合成。研究提出了合理的反应机理：二氯碘苯(PhICl2)与硒氰酸钾(KSeCN)先原位生成活性Cl-SeCN中间体，随后发生涉及C-N键与C-Se键构建的级联环化过程。