Arene Trifunctionalization with Highly Fused Ring Systems through Domino Aryne Nucleophilic, Diels-Alder Cascade.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2019)
摘要
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.
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关键词
arenes,arynes,benzdiynes,domino reactions,fused ring systems
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