Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 23, Pages 11706-11717Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01014
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Funding
- National Science Foundation [CHE-1465142]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1465142] Funding Source: National Science Foundation
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The majority of Sn-mediated cydizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an allcyne where ALBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.
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