1839-72-1Relevant articles and documents
Insight into the palladium-catalyzed oxidative arylation of benzofuran: Heteropoly acid oxidants evoke a Pd(II)/Pd(IV) mechanism
Pereira, Kyle C.,Porter, Ashley L.,Potavathri, Shathaverdhan,Lebris, Alexis P.,Deboef, Brenton
, p. 4429 - 4435 (2013)
The effects of oxidant and organic acid additives on the oxidative cross-coupling reactions of electron rich heterocycles, such as benzofuran with benzene were studied. Both regioselectivity and reaction rate could be controlled by varying the condition p
Pd(II)-β-cyclodextrin complex: Synthesis, characterization and efficient nanocatalyst for the selective Suzuki-Miyaura coupling reaction in water
Kaboudin, Babak,Salemi, Hadi,Mostafalu, Ramin,Kazemi, Foad,Yokomatsu, Tsutomu
, p. 195 - 199 (2016)
Herein we report the preparation, characterization and the catalytic ability of novel Pd(II)-β-cyclodextrin complex as an efficient nanocatalytic system for the Suzuki-Miyaura carbon-carbon (C-C) coupling reaction in water. The presented novel Pd(II)-β-cyclodextrin complex catalyst was characterized by TGA, FT-IR, XRD, NMR and atomic absorption analysis. Also, by using the Pd(II)-β-CD complex as a homogeneous catalyst, we have developed an efficient protocol for suzuki-Miyaura coupling reaction of aryl boronic acids with aryl halides in neat water with high turnover frequencies (TOFs) for the synthesis of unsymmetrical biaryls. The catalyst can be recycled and reused multiple times to catalyze the coupling reaction.
Kinetics and mechanism of phosphate photorelease from benzoin diethyl phosphate: Evidence for adiabatic fission to an α-keto cation in the triplet state
Rajes, Cheruvallil S.,Givens, Richard S.,Wirz, Jakob
, p. 611 - 618 (2000)
The photodissociation of benzoin diethyl phosphate (1, 'caged' phosphate) was studied by nanosecond and picosecond laser flash photolysis. The lowest triplet state of 1, 31, was identified as the reactive excited state with an absorption maximum around 340 nm and a lifetime of 10-25 ns, depending on the solvent. Two different reaction paths were identified, both of which involve the release of diethyl phosphoric acid from 31 within 25 ns. In addition to a fast cyclization-elimination process leading to 2- phenylbenzofuran (2) and diethyl phosphoric acid, heterolytic adiabatic dissociation of 31 yields a triplet cation and diethyl phosphate anion in water, trifluoroethanol, and hexafluoro-2-propanol solutions. The triplet cation (570 nm, τ ? 430 ns in water) undergoes intersystem crossing to the singlet ground state before it reacts with the solvent molecules.
Photolabile benzoin and furoin esters of a biologically active peptide
Peach, Josephine M.,Pratt, Andrew J.,Snaith, John S.
, p. 10013 - 10024 (1995)
Benzoin and furoin esters of N-carbobenzyloxyglycylphenylalanine were prepared and photolyzed under a variety of conditions. The photochemistry of peptide-derived benzoin esters is more efficient than that of furoin esters and is appropriate for the photo
Synthesis of fused and linked benzofurans from 2-alkynylphenol derivatives through rhodium(i)-catalyzed domino-type addition reactions
Matsuda, Takanori,Abe, Shinya,Ito, Hirotaka,Tsuboi, Tomoya,Kirikae, Haruki,Murakami, Masahiro
, p. 888 - 891 (2018)
A rhodium(i)-catalyzed domino-type sequential 5-endo/5-exo cyclization reaction of [(2-acylphenyl) ethynyl]phenols produces indene/benzofuran-fused alcohols. A moderate asymmetric induction is observed when chiral diphosphine ligands are used for rhodium.
A stereoselective synthesis of 1,2-diarylethenyl ethyl ethers via the carbocupration-cross coupling sequence
Kato, Noriyasu,Miyaura, Norio
, p. 13347 - 13354 (1996)
The synthesis of vinyl ethers [Ph(EtO)C= CHAr] was carried out by a sequence of carbocupration of ethoxyethyne with phenylcopper(I) followed by the palladium-catalyzed crosscoupling reaction of the resulting 2-ethoxyvinylcopper(I) complex with iodoarenes. The 2-ethoxyvinylcopper(I) species thus obtained were sufficiently stable to undergo the cross-coupling reaction at 0-20°C in the presence of a catalytic amount of PdCl2(dppf) or Pd(PPh3)4 and 1 equivalent of ZnBr2. The syntheses of 2-phenylbenzo[b]furan and 2-phenylindole demonstrated the utility of the present one-pot, two-step procedure for the synthesis of vinyl ethers.
A highly Lewis-acidic Pd(iv) surface on Pd@SiO2 nanocatalysts for hydroalkoxylation reactions
Kim, Mijong,Lee, Suyeon,Kim, Kiseong,Shin, Dongwoo,Kim, Hyunwoo,Song, Hyunjoon
, p. 14938 - 14941 (2014)
The Pd(iv) species, known to be critical intermediates in homogeneous catalysis, were successfully generated on the surface of Pd nanocatalysts via oxidation with iodobenzene dichloride (PhICl2) or N-chlorosuccinimide (NCS). In particular, the
Mild and efficient cyclization reaction of 2-ethynylaniline derivatives to indoles in aqueous medium
Hiroya, Kou,Itoh, Shin,Sakamoto, Takao
, p. 10958 - 10964 (2005)
Results of the optimized cyclization reaction of 2-ethynylaniline derivatives to indoles catalyzed by copper(II) salts are described. The reactions can be carried out in a mixture of H2O and MeOH in the presence of 1-ethylpiperidine at room tem
2,3-Disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole
Nakamura, Masaharu,Ilies, Laurean,Otsubo, Saika,Nakamura, Eiichi
, p. 2803 - 2805 (2006)
A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl2 produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.
Novel cyclization to benzofurans in the reaction of alkynyl(p-phenylene) bisiodonium ditriflates with phenoxide anion
Kitamura, Tsugio,Zheng, Lei,Taniguchi, Hiroshi,Sakurai, Makoto,Tanaka, Ryuichi
, p. 4055 - 4058 (1993)
Reaction of alkynyl(p-phenylene)bisiodonium ditriflates (2) with sodium phenoxide in methanol provides 2-substituted benzofurans (3). This result indicates that β-phenoxyalkylidenecarbenes generated by the reaction with phenoxide anion undergo novel intramolecular aromatic C-H insertion to afford benzofurans.
