81206-47-5Relevant academic research and scientific papers
Condensed heteroaromatic ring systems. XVII. Palladium-catalyzed cross-coupling reaction of aryl bromides with (Z)-1-ethoxy-2-tributylstannylethene and its utilization for construction of condensed heteroaromatics
Sakamoto,Kondo,Yasuhara,Yamanaka
, p. 1877 - 1886 (2007/10/02)
The palladium-catalyzed cross-coupling reaction of bromobenzenes or bromoheteroarenes such as pyridine, thiophene, indole with (Z)-1-ethoxy-2-tributylstannylethene gives good yields of the corresponding (Z)-1-ethoxy-2-(aryl and heteroaryl)ethenes. This method is effective for introducing an ethoxyethenyl group into an aromatic and heteroaromatic ring and is proved to have versatile utility for the construction of benzo[b]furan, indole, isocoumarin rings 2-bromophenol, 2-bromoaniline, and 2-bromobenzoate derivatives.
Palladium-Catalyzed Cross-Coupling of (2-Ethoxyvinyl)boranes with Aryl and Benzyl Halides. A New Method for Conversion of Organic Halides into Aldehydes with Two More Carbon Atoms
Miyaura, Norio,Maeda, Koji,Suginome, Hiroshi,Suzuki, Akira
, p. 2117 - 2120 (2007/10/02)
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.
