Journal of Organic Chemistry p. 2117 - 2120 (1982)
Update date:2022-08-04
Topics:
Miyaura, Norio
Maeda, Koji
Suginome, Hiroshi
Suzuki, Akira
Vinyl ethers 3 can be synthesized in high yields by the cross-coupling of an aryl or benzyl halide with tris(2-ethoxyvinyl)borane (1) or (2-ethoxyvinyl)-1,3,2-benzodioxaborole (2) in the presence of 1 mol percent of a palladium complex such as PdCl2(PPh3)2, Pd(OAc)2(PPh3)2, or Pd(PPh3)4 and a base while retaining the original configuration of the double bond in (2-ethoxyvinyl)boranes.No noticeable quantities of biaryls or conjugated dienes were found in this reaction.The reaction did not proceed in the absence of a base.This new vinyl ether synthesis was found to be applicable to aryl halides substituted with a variety of functional groups such as halogen, methoxy, carboethoxy, and acetyl groups.Electron-attracting substituents facilitate the coupling.Since vinyl ethers 3 thus obtained can readily be hydrolyzed to give aldehydes (eq 4), the sequence (eq 1-4) provides an efficient new method for converting an aryl halide into an aldehyde with two more carbon atoms.
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