Premium
Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
Author(s) -
He Jia,
Jia Zizi,
Tan Hongcheng,
Luo Xiaohua,
Qiu Dachuan,
Shi Jiarong,
Xu Hai,
Li Yang
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201911730
Subject(s) - aryne , moiety , domino , chemistry , ring (chemistry) , cascade reaction , nucleophile , cascade , nucleophilic addition , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , chromatography , catalysis
A convenient and efficient domino aryne process was developed under transition‐metal‐free conditions to generate a range of tetra‐ and pentacyclic ring systems. This transformation was realized via a 1,2‐benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C−N and two C−C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2‐aryne and 2,3‐aryne stages. Moreover, in‐depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.