Synthesis of Diiodinated All-Carbon 3,3 '-Diphenyl-1,1 '-ispirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution

Li, Quanzhe1,2; Yu, Liuzhu1,2; Wei, Yin3; Shi, Min1,2,3,4

2019-07-19

10.1021/acs.joc.9b01418

JOURNAL OF ORGANIC CHEMISTRY   影响因子和分区

0022-3263

1520-6904

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.

SCI ; EI ; IC ; CCR

英语

通讯

Fundamental Research Funds for the Central Universities[222201717003]

Chemistry

Chemistry, Organic

WOS:000476957000042

AMER CHEMICAL SOC

20193207283512

Aromatic hydrocarbons ; Substitution reactions

Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

Web of Science

1.East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China
2.East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Organometall Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
4.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Li, Quanzhe,Yu, Liuzhu,Wei, Yin,et al. Synthesis of Diiodinated All-Carbon 3,3 '-Diphenyl-1,1 '-ispirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(14):9282-9296.

Li, Quanzhe,Yu, Liuzhu,Wei, Yin,&Shi, Min.(2019).Synthesis of Diiodinated All-Carbon 3,3 '-Diphenyl-1,1 '-ispirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution.JOURNAL OF ORGANIC CHEMISTRY,84(14),9282-9296.

Li, Quanzhe,et al."Synthesis of Diiodinated All-Carbon 3,3 '-Diphenyl-1,1 '-ispirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution".JOURNAL OF ORGANIC CHEMISTRY 84.14(2019):9282-9296.