Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 21, Pages 14161-14167Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01644
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Funding
- University Grants Commission (UGC)
- Council of Industrial and Scientific Research (CSIR), India
- SERB, New Delhi, India [CRG/2018/004424]
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A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from beta-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.
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