Synthesis and Stability of o-Carborane-Fused Phospholes DOI
Caixia Jia, Lili Wang, Zheng Duan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Herein, we report that ArLi, formed in situ through the Li/Br exchange between aryl bromide and n-butyllithium, can undergo rapid intramolecular Li/H(Ccage–H) to functionalize o-carboranes. Based on this observation, a dual C–H lithiation reaction of 2- or 3-o-carboryl benzothiophenes was developed, series o-carborane-fused phospholes were synthesized by dilithio compounds with chlorophosphine. This is simple high chemical selectivity medium yields. It also be applied furan derivative. Stability studies demonstrated these phosphole derivatives are stable both trivalent coordination states for phosphorus. In contrast, their oxides sensitive moisture air susceptible attack nucleophiles, leading breakage Ccage-P bond. Computational results indicate newly generated rings have weak aromaticity.

Language: Английский

Synthesis and Stability of o-Carborane-Fused Phospholes DOI
Caixia Jia, Lili Wang, Zheng Duan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Herein, we report that ArLi, formed in situ through the Li/Br exchange between aryl bromide and n-butyllithium, can undergo rapid intramolecular Li/H(Ccage–H) to functionalize o-carboranes. Based on this observation, a dual C–H lithiation reaction of 2- or 3-o-carboryl benzothiophenes was developed, series o-carborane-fused phospholes were synthesized by dilithio compounds with chlorophosphine. This is simple high chemical selectivity medium yields. It also be applied furan derivative. Stability studies demonstrated these phosphole derivatives are stable both trivalent coordination states for phosphorus. In contrast, their oxides sensitive moisture air susceptible attack nucleophiles, leading breakage Ccage-P bond. Computational results indicate newly generated rings have weak aromaticity.

Language: Английский

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