Revisiting the Synthetic Utility of 4,5‐Dehydro[2.2]paracyclophane DOI Creative Commons
Jumpei Taguchi,

Yusuke Omoto,

Kensaku Uto

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 22, 2024

Abstract 4,5‐Dehydro[2.2]paracyclophane, an aryne species of [2.2]paracyclophane ([2.2]PCP) was reported more than half a century ago. However, despite its potential usefulness for preparing [2.2]PCP derivatives, this is rarely considered in synthetic applications, probably because the efficiency generation and reaction with arynophiles are low under harsh conditions classical methods involving precursors. We have prepared o ‐iodoaryl triflate‐ ‐silylaryl triflate‐type precursors achieved 4,5‐dehydro[2.2]PCP, which reacted diverse range to afford functionalized including [2.2]PCP‐fused π‐extended polyaromatics. Our results highlight utility historically overlooked 4,5‐dehydro[2.2]PCP intermediate.

Language: Английский

Revisiting the Synthetic Utility of 4,5‐Dehydro[2.2]paracyclophane DOI Creative Commons
Jumpei Taguchi,

Yusuke Omoto,

Kensaku Uto

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 22, 2024

Abstract 4,5‐Dehydro[2.2]paracyclophane, an aryne species of [2.2]paracyclophane ([2.2]PCP) was reported more than half a century ago. However, despite its potential usefulness for preparing [2.2]PCP derivatives, this is rarely considered in synthetic applications, probably because the efficiency generation and reaction with arynophiles are low under harsh conditions classical methods involving precursors. We have prepared o ‐iodoaryl triflate‐ ‐silylaryl triflate‐type precursors achieved 4,5‐dehydro[2.2]PCP, which reacted diverse range to afford functionalized including [2.2]PCP‐fused π‐extended polyaromatics. Our results highlight utility historically overlooked 4,5‐dehydro[2.2]PCP intermediate.

Language: Английский

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