(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenyl → 4-(Ethynyloxy)-1,1'-biphenyl

HRID 1053509

Reaction equation

HRID 1053509 reaction equation
[Li]CCCC.I/[CH:7]=[CH:8]/[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>[Cu]>[C:8]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)#[CH:7]

Participants

4

Reactant 2

HCID 89873752(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenylHCID 178418339Butyllithium

Product 1

HCID 698274994-(Ethynyloxy)-1,1'-biphenylYield 70%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

For the synthesis of the 1,2-diheteroatom-substituted olefins (See Scheme 3), four-step scheme was developed where 4-phenylphenol 1 was used in one side. First, 4-phenylphenol was vinylated using 1,1,2-trichloroethylene45 to give the corresponding 4-((1,2-dichlorovinyl)oxy)-1,1′-biphenyl 2 with yield of more than 85%.46, 47 Then, 4-(ethynyloxy)-1,1′-biphenyl 3 was prepared by elimination reaction using n-BuLi in 70% yield.46,47 Although 1 was used in this paper, other types of alcohols and phenols can also be converted to the alkyne form.46 Hydrozirconation and iodinolysis of 3 led to 2-iodoenol ether 4 in 55% yield.48, 49 Using the copper-catalyzed coupling reaction, 4 were linked with various substrates bearing the different functional groups.36,50, 51

Workup

  1. customreaction, 4

Sources & evidence

ORD record
ord-c88a7dfef3274d81acd9cfed4b9cab32
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Linked notes

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