65246-49-3Relevant academic research and scientific papers
Palladium-catalyzed reaction of arylboronic acids with aliphatic nitriles: Synthesis of alkyl aryl ketones and 2-arylbenzofurans
Wang, Xingyong,Wang, Xiaodong,Liu, Miaochang,Ding, Jinchang,Chen, Jiuxi,Wu, Huayue
, p. 2241 - 2244 (2013)
An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions. Georg Thieme Verlag Stuttgart. New York.
Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: From alkynes to benzo[b]furans and benzo[b]thiophenes
Li, Yibiao,Cheng, Liang,Liu, Xiaohang,Li, Bin,Sun, Ning
supporting information, p. 2886 - 2891 (2015/02/19)
An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b ] furan and benzo[ b ] thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves
One-Pot preparation of 2-arylbenzofurans from oximes with diaryliodonium triflate
Miyagi, Kotaro,Moriyama, Katsuhiko,Togo, Hideo
, p. 2122 - 2136 (2015/01/09)
A variety of 2-arylbenzofurans were obtained in good yields by the O-arylation of oximes with diaryliodonium triflates, followed by the treatment with HCl in dioxane under warming conditions through the [3,3]-sigmatropic reaction. The present reaction is one-pot transition metal-free method for the preparation of various 2-arylbenzofurans from oximes, which are easily available from the reaction of alkyl aryl ketones with hydroxylamine.
Palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles: Synthesis of alkyl aryl ketones, diketone compounds, and 2-arylbenzo[b]furans
Wang, Xingyong,Liu, Miaochang,Xu, Long,Wang, Qingzong,Chen, Jiuxi,Ding, Jinchang,Wu, Huayue
, p. 5273 - 5281 (2013/07/26)
A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential addition and intramolecular annulation reactions. The methodology accepted a wide range of substrates and is applicable to library synthesis.
Chemoselectivity control: Gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7- oxabicyclo[4.1.0]heptan-2-ones
Wang, Tao,Shi, Shuai,Vilhelmsen, Mie Hojer,Zhang, Tuo,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 12512 - 12516 (2013/09/23)
New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products - 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans - could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2- ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments. Complete chemoselectivity control of gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]heptan- 2-ones, which can be achieved by changing the ligand of the gold catalyst, allows two different products to be obtained from the same starting material, namely, 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans (see scheme), both of which are potent building blocks for synthetic chemistry. IPr: 1,3-bis(diisopropylphenyl)imidazol-2-ylidene. Copyright
Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations
Baxendale, Ian R.,Griffiths-Jones, Charlotte M.,Ley, Steven V.,Tranmer, Geoffrey K.
, p. 4407 - 4416 (2008/02/07)
This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-en-capsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused microwave heating whilst applying an external cooling source. This enables a lower than normal bulk temperature to be maintained throughout the reaction period leading to significant improvements in the overall yield and purity of the reaction products. Additional aspects of this novel heating protocol are discussed in relation to the prolonged lifetime and enhanced reactivity of the immobilised catalyst system.
