Efficient Synthesis of 2-Mono- and 2,5-Disubstituted Furans via the CuI-Catalyzed Cycloisomerization of Alkynyl Ketones

• Published in: Journal of organic chemistry Vol. 67; no. 1; pp. 95 - 98
• Main Authors: Kel'i, Alexander V, Gevorgyan, Vladimir
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 11.01.2002; Amer Chemical Soc
• Subjects: Alkynes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper; Cyclization; Exact sciences and technology; Furans - chemical synthesis; Furans - chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Iodides; Isomerism; Ketones - chemistry; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; REARRANGEMENT; ALCOHOLS; CARBONYLATION; REAGENTS; ALLENONES; ESTERS; COPPER; SUBSTITUTED FURANS; CYCLIZATION; (Z)-2-EN-4-YN-1-OLS; Five membered ring; Catalytic reaction; Acetylenic compound; Cyclization; Copper iodide; Furan derivatives; Ynone; Oxygen heterocycle; Chemical synthesis; Ketone
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo010832v

A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.