Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 51, Pages 18513-18518Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911730
Keywords
arenes; arynes; benzdiynes; domino reactions; fused ring systems
Categories
Funding
- NSFC [21772017]
- Basic and Frontier Research Project of Chongqing [cstc2018jcyjAX0357]
- Fundamental Research Funds for the Central Universities [2018CDXZ0003]
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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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