Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes

• Published in: Chemical communications (Cambridge, England) Vol. 56; no. 77; pp. 11429 - 11432
• Main Authors: Liang, Hao, He, Xiaobo, Zhang, Yaqi, Chen, Bin, Ouyang, Jia-sheng, Li, Yongsu, Pan, Bendu, Subba Reddy, Chitreddy V, Chan, Wesley Ting Kwok, Qiu, Liqin
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 29.09.2020; Royal Society of Chemistry
• Subjects: Alkynes; Carboxylates; Chemistry; Chemistry, Multidisciplinary; Copper; Copper compounds; Crystallography; diazo compounds; Physical Sciences; Reaction mechanisms; Science & Technology; PHENYLDIMEDONYLIODONE; HETEROCYCLES; ANNULATION; ARYLATION; EFFICIENT SYNTHESIS; CHEMISTRY; DIARYLIODONIUM; CYCLOISOMERIZATION; PHENYLIODONIUM YLIDES; AROMATIC-COMPOUNDS
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d0cc04373g

The copper( ii )-catalyzed (4+1) cyclizations and copper( i )-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionalized dimethyl ( E )-3-benzylideneindoline-2,2-dicarboxylates and methyl 5-(2-hydroxyphenyl)-2-methoxy-4-phenylfuran-3-carboxylates were conveniently prepared in moderate to excellent yields. The possible reaction mechanisms were also discussed. The copper( ii )-catalyzed (4+1) cyclizations and copper( i )-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes have been successfully developed. The corresponding highly functionalized heterocyclic products were prepared conveniently.