1207-95-0Relevant articles and documents
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Schrauzer,Mayweg
, p. 3221 (1962)
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Suzuki-type cross-coupling reaction of pentavalent triarylantimony diacetates with arylboronic acids without a base
Yasuike, Shuji,Qin, Weiwei,Sugawara, Yoshiyuki,Kurita, Jyoji
, p. 721 - 724 (2007)
Novel base-free Suzuki-type cross-coupling reaction by the use of triarylantimony diacetates and arylboronic acids in the presence of Pd(PPh3)4 catalyst led to the formation of biaryl derivatives in moderate to excellent yields. The reaction is applicable to a variety of arylboronic acids bearing base-sensitive functional groups.
Room-temperature Pd/Ag direct arylation enabled by a radical pathway
Luscombe, Christine K.,Mayhugh, Amy L.
, p. 384 - 390 (2020)
Direct arylation is an appealing method for preparing π-conjugated materials, avoiding the prefunctionalization required for traditional cross-coupling methods. A major effort in organic electronic materials development is improving the environmental and economic impact of production; direct arylation polymerization (DArP) is an effective method to achieve these goals. Room-temperature polymerization would further improve the cost and energy efficiencies required to prepare these materials. Reported herein is new mechanistic work studying the underlying mechanism of room temperature direct arylation between iodobenzene and indole. Results indicate that room-temperature, Pd/Ag-catalyzed direct arylation systems are radical-mediated. This is in contrast to the commonly proposed two-electron mechanisms for direct arylation and appears to extend to other substrates such as benzo[b]thiophene and pentafluorobenzene.
A simple phenylation of heteroaromatic compounds using diphenyliodonium triflate
Yang, Qi,Chang, Jiao,Wu, Qun,Zhang, Bianxiang
, p. 1335 - 1340 (2012)
In this study a novelmethod for direct synthesis of 2-phenyl heteroaromatic arenes was successfully developed. The title compounds were synthesized by reaction of heteroaromatic compoundswith diphenylene iodonium trifluoromethanesulfonate in the presence of 5 mol% Pd(OAc)2 under mild reaction conditions (THF, 60 °C, 24 h). The proposed reaction mechanism was studied by HPLC. Springer Science+Business Media B.V. 2011.
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Malte,Castro
, p. 6770 (1967)
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Asymmetric Cyclizative Dimerization of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst
Peng, Cheng,Kusakabe, Taichi,Kikkawa, Shoko,Mochida, Tomoyuki,Azumaya, Isao,Dhage, Yogesh Daulat,Takahashi, Keisuke,Sasai, Hiroaki,Kato, Keisuke
, p. 733 - 737 (2019)
The first example of an asymmetric cyclization–dimerization of (ortho-alkynyl phenyl) (methoxymethyl) sulfides with a palladium(II) bisoxazoline (box) catalyst has been developed. The box ligand enhances the alkynophilicity of benzothienyl palladium(II) intermediate A and thus promotes coordination of the second alkyne substrate, leading to the dimerization. The characteristic properties of the box ligand were supported by density functional theory (DFT) calculations of the intermediate. Axially chiral bibenzothiophenes were obtained in good yields with good enantioselectivities.
Infrared Irradiation-Assisted Solvent-Free Pd-Catalyzed (Hetero)aryl-aryl Coupling via C?H Bond Activation
Albano, Gianluigi,Decandia, Gianfranco,Capozzi, Maria Annunziata M.,Zappimbulso, Nicola,Punzi, Angela,Farinola, Gianluca M.
, p. 3391 - 3401 (2021)
The increasing attention towards environmentally friendly synthetic protocols has boosted studies directed to the development of green and sustainable methods for direct C?H bond arylation of (hetero)arenes. In this context, here the infrared (IR) irradia
Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction
Pivsa-Art, Sommai,Satoh, Tetsuya,Kawamura, Yoshiki,Miura, Masahiro,Nomura, Masakatsu
, p. 467 - 473 (1998)
The reactions of iodobenzene with azole compounds, 1,2-disubstituted imidazoles and 2-substituted oxazoles and thiazoles, were examined in the presence of catalytic amounts of Pd(OAc)2 and PPh3 in DMF using alkali metal carbonates as bases. It was found that the coupling products, 5-arylazoles, could be selectively produced in good yields by using CS2CO3. In the case that their 2-position is unsubstituted, the site could also be arylated. In reactions using bromobenzene in place of iodobenzene, K2CO3 was also as effective as Cs2CO3- The addition of a stoichiometric amount of Cul appeared to specifically promote the reactions of thiazoles as well as those of thiophene derivatives. The reactions of 2-unsubstituted azole compounds with aryl iodides could be mediated by Cul to some extent without using the palladium species to give 2-arylazoles.
Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): an efficient catalyst for regioselective C-2 arylation of heterocycles
Nandurkar, Nitin S.,Bhanushali, Mayur J.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
, p. 1045 - 1048 (2008)
Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate), a structurally well defined O-containing transition metal complex is reported as an efficient catalyst for regioselective direct C-2 arylation of heterocycles with aryl halides. The present protocol is applicable to a wide variety of heterocycles providing good to excellent yields of products.
Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
supporting information, p. 10242 - 10245 (2021/10/12)
Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
Metalated Porous Phenanthroline-Based Polymers as Efficient Heterogeneous Catalysts for Regioselective C?H Activation of Heteroarenes
Tang, Yongquan,Dai, Zhifeng,Wang, Sai,Chen, Fang,Meng, Xiangju,Xiao, Feng-Shou
, p. 2469 - 2474 (2021/08/06)
Direct C?H bond activation of heterocycles as a step-economical and environmentally friendly approach to build the heterobiaryls motifs is highly attractive, but it still has a challenge to design and prepare a cheap and regioselective heterogeneous catal
