939792-77-5Relevant academic research and scientific papers
Nickel-Catalyzed Amination of α-Aryl Methyl Ethers
Patel, Purvish,Rousseaux, Sophie A. L.
, p. 492 - 496 (2020/03/13)
α-Aryl amines are prevalent in pharmaceutically active compounds and natural products. Herein, we describe a Ni-catalyzed protocol for their synthesis from readily available α-aryl ethers. While α-aryl ethers have been used as electrophiles in Ni-catalyzed C-C bond formations, their use in C-heteroatom bond formation is much less prevalent. Preliminary mechanistic insight suggests that oxidative addition is facilitated by an anionic ligand and that reductive elimination is a reversible process.
A recyclable palladium-catalyzed synthesis of 2-methylene-2,3- dihydrobenzofuran-3-ols by cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols in ionic liquids
Mancuso, Raffaella,Gabriele, Bartolo
, p. 10901 - 10911 (2013/10/22)
A recyclable palladium-catalyzed synthesis of 2-methylene-2,3- dihydrobenzofuran-3-ols 2 by heterocyclization of 2-(1-hydroxyprop-2-ynyl) phenols 1 in an ionic liquid medium (BmimBF4) is presented. The process takes place under relativelyn mild conditions (100 °C, 5 h) in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (5 equiv with respect to PdI2) and an organic base, such as morpholine (1 equiv with respect to 1), to give 2 in high yields (70%-86%). The PdI 2-KI catalytic system could be recycled up to six times without appreciable loss of activity. Moreover, products 2 could be easily converted in a one-pot fashion into 2-hydroxymethylbenzofurans 3 (52%-71%, based on 1) and 2-methoxymethylbenzofurans 4 (52%-80%, based on 1) by acid-catalyzed allylic isomerization or allylic nucleophilic substitution.
A new copper(I)-catalyzed cycloetherification/acid-catalyzed allylic nucleophilic substitution for one-pot synthesis of 2-substituted benzofurans
Li, Xin,Xue, Jijun,Chen, Rui,Li, Ying
supporting information; experimental part, p. 1043 - 1046 (2012/06/04)
A new copper(I)-catalyzed cycloetherification followed by an acid-catalyzed allylic nucleophilic substitution have been developed for the one-pot synthesis of 2-substituted benzofurans. This one-pot reaction proceeds efficiently under extremely mild conditions with simple and inexpensive catalysts, providing diversely substituted benzofurans in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.
A novel synthesis of 2-functionalized benzofurans by palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols followed by acid-catalyzed allylic isomerization or allylic nucleophilic substitution
Gabriele, Bartolo,Mancuso, Raffaella,Salerno, Giuseppe
supporting information; experimental part, p. 7336 - 7341 (2009/04/18)
(Chemical Equation Presented) A novel two-step synthesis of 2-hydroxymethylbenzofurans 3 and 2-alkoxymethylbenzofurans 4-6, based on palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols 1 under basic conditions to give 2-methylene-2,3-dihydrobenzofuran-3-ols 2, followed by acid-catalyzed isomerization or allylic nucleophilic substitution with alcohols as nucleophiles, is reported. Cycloisomerization reactions leading to 2 (80-98% yields) were carried out at 40°C in MeOH as the solvent, in the presence of a base and catalytic amounts of PdX2 + 2KX (X = Cl, I). Isomerization reactions of 2 readily occurred at 25-60 °C in DME as the solvent, with H2SO4 as the proton source, to give 2-hydroxymethylbenzofurans 3 in 65-90% yields. In a similar manner, allylic nucleophilic substitution reactions of 2 with ROH as nucleophiles [carried out at 25-40°C in ROH (R = Me) or ROH-DME mixtures (R = Bu, Bn) in the presence of H2SO4] afforded 2-alkoxymethylbenzofurans 4, 5, and 6 (R = Me, Bu, and Bn, respectively), in 65-98% yields.
A facile approach to the synthesis of chiral 2-substituted benzofurans
De Luca, Lidia,Giacomelli, Giampaolo,Nieddu, Giammario
, p. 3955 - 3957 (2008/02/01)
(Chemical Equation Presented) An effective route to chiral optically active 2-substituted benzofurans directly from carboxylic acids is reported. This procedure, which allows the preparation of α-alkyl-2- benzofuranmethanamines from N-protected α-amino ac
Dearomatization of furans via [2,3]-Still-Wittig rearrangement
Caruana, Patrick A.,Frontier, Alison J.
, p. 10921 - 10926 (2007/10/03)
Furans and benzofurans of type 1 were dearomatized via the [2,3]-Still-Wittig rearrangement. Enol ethers 2 could be isolated or isomerized to the corresponding furans 3. The substitution pattern at the homofuranylic position had a strong influence on reaction behavior. Benzofurans rearranged with the greatest efficiency, and employment of a 3-substituted benzofuran (1; R′=CH3) allowed the creation of a quaternary carbon center.
