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

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Reaction Steps

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

Provenance & Evidence