Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution.
J Org Chem. 2019 Jul 19; 84(14):9282-9296.JO

Abstract

A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.

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Authors+Show Affiliations

Li Q

Yu L

Wei Y

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling-Ling Road , Shanghai , 200032 , China.

Shi M

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering , East China University of Science and Technology , 130 Meilong Road , Shanghai 200237 , China. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling-Ling Road , Shanghai , 200032 , China. Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , Guangdong 518000 , China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31257888

Citation

Li, Quanzhe, et al. "Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives Via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution." The Journal of Organic Chemistry, vol. 84, no. 14, 2019, pp. 9282-9296.

Li Q, Yu L, Wei Y, et al. Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution. J Org Chem. 2019;84(14):9282-9296.

Li, Q., Yu, L., Wei, Y., & Shi, M. (2019). Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution. The Journal of Organic Chemistry, 84(14), 9282-9296. https://doi.org/10.1021/acs.joc.9b01418

Li Q, et al. Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives Via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution. J Org Chem. 2019 Jul 19;84(14):9282-9296. PubMed PMID: 31257888.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution. AU - Li,Quanzhe, AU - Yu,Liuzhu, AU - Wei,Yin, AU - Shi,Min, Y1 - 2019/07/11/ PY - 2019/7/2/pubmed PY - 2019/7/2/medline PY - 2019/7/2/entrez SP - 9282 EP - 9296 JF - The Journal of organic chemistry JO - J Org Chem VL - 84 IS - 14 N2 - A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/31257888/Synthesis_of_Diiodinated_All_Carbon_33'_Diphenyl_11'_spirobiindene_Derivatives_via_Cascade_Enyne_Cyclization_and_Electrophilic_Aromatic_Substitution_ DB - PRIME DP - Unbound Medicine ER -

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Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution.J Org Chem. 2019 Jul 19; 84(14):9282-9296.JO