Details

Autor(en) / Beteiligte

• Su, Lebin
• Xie, Shimin
• Dong, Jianyu
• Pan, Neng
• Yin, Shuang-Feng
• Zhou, Yongbo

Titel

Copper-Catalyzed 6-endo-dig Cyclization–Coupling of 2‑Bromoaryl Ketones and Terminal Alkynes toward Naphthyl Aryl Ethers in Water

Ist Teil von

• Organic letters, 2022-07, Vol.24 (25), p.4569-4574

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The cyclization–coupling reaction of 2-bromoaryl ketones and terminal alkynes is first realized by copper catalysis, which produces polyfunctional naphthyl aryl ethers in moderate to excellent yields with broad substrate scope and good functional group tolerance. This reaction proceeds via 6-endo-dig cyclization and C­(sp2)–O coupling using green H2O as the unique solvent and 5-bromopyrimidin-2-amine as the critical additive. Mechanistically, a unique Cu­(III)-acetylide probably is the key intermediate, which allows exclusive 6-endo-dig selectivity.