- Nickel-Catalyzed Reductive Cleavage of Carbon-Oxygen Bonds in Anisole Derivatives Using Diisopropylaminoborane
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The catalytic removal of a methoxy group on an aromatic ring allows this group to be used as a traceless activating and directing group for aromatic functionalization reactions. Although several catalytic methods for the reductive cleavage of anisole derivatives have been reported, all are applicable only to π-extended aryl ethers, such as naphthyl and biphenyl ethers, while monocyclic aryl ethers cannot be reduced. Herein, we report a nickel-catalyzed reductive cleavage reaction of C-O bonds in aryl ethers using diisopropylaminoborane as the reducing agent. Unlike previously reported methods, this reducing reagent allows effective C-O bond reduction in a much wider range of aryl ether substrates, including monocyclic and heterocyclic ethers bearing various functional groups.
- Igarashi, Takuya,Haito, Akira,Chatani, Naoto,Tobisu, Mamoru
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p. 7475 - 7483
(2018/07/21)
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- The reduction of aryl diethyl phosphate esters with lithium di-tert-butylbiphenylide radical anion: Aromatic hydrocarbons via the deoxygenation of phenols
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The reduction of aryl diethyl phosphate esters by lithium 4,4′-di-tert-butylbiphenylide (LiDTBB) in THF at 0 °C is described. The reactions can be carried out either stoichiometrically (3.0 equiv LiDTBB) or with only a catalytic amount of DTBB (0.25 equiv) in the presence of lithium (2.1-3.0 equiv) and the phosphate. Products are separated from DTBB by solubility differences, by acid/base vs. neutral extraction, or by flash chromatography.
- Lusch, Michael J.,Woller, Kevin R.,Keller, Anthony M.,Turk, Michael C.
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p. 551 - 554
(2007/10/03)
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