Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes

Liu, Jiaxin1; Wei, Yin1; Shi, Min1,2

2021-01-07

10.1039/d0qo00853b

Organic Chemistry Frontiers   影响因子和分区

2052-4129

We report a direct single-electron oxidation of methylenecyclopropanes (MCPs) for the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives by merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N center dot 3HF (1.0 equiv.), the fluorination of MCPs can be realized in the presence of 9-mesityl-10-methylacridinium perchlorate and Co(dmgH)(2)PyCl, affording fluorinated 4-aryl-1,2-dihy-dronaphthalene derivatives in moderate yields. In MeCN/HFIP (7 : 3), 4-aryl-1,2-dihydronaphthalene derivatives were obtained in good yields through a MHAT process under similar conditions.

SCI ; IC ; CCR ; EI

英语

通讯

Strategic Priority Research Program of the Chinese Academy of Sciences[XDB20000000] ; National Natural Science Foundation of China[21372250,21121062,21302203,20732008,21772037,21772226,21861132014,91956115] ; [sioczz201808]

Chemistry

Chemistry, Organic

WOS:000605450500012

ROYAL SOC CHEMISTRY

20210209756377

Catalysis ; Inorganic compounds ; Propane

Light/Optics:741.1 ; Chemical Reactions:802.2 ; Inorganic Compounds:804.2

Web of Science

1.Chinese Acad Sci, Shanghai Inst Organ Chem, Univ Chinese Acad Sci, Ctr Excellence Mol Synth,State Key Lab Organometa, 345 Lingling Rd, Shanghai 200032, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Liu, Jiaxin,Wei, Yin,Shi, Min. Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes[J]. Organic Chemistry Frontiers,2021,8(1):94-100.

Liu, Jiaxin,Wei, Yin,&Shi, Min.(2021).Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes.Organic Chemistry Frontiers,8(1),94-100.

Liu, Jiaxin,et al."Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes".Organic Chemistry Frontiers 8.1(2021):94-100.