1207-95-0Relevant articles and documents
Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics
Morofuji, Tatsuya,Shimizu, Akihiro,Yoshida, Jun-Ichi
, p. 9816 - 9819 (2015)
A new approach for electrooxidative coupling of aromatic compounds and primary alkylamines bearing a functional group such as a hydroxyl group and an amino group was developed. The key to the success of the transformation is heterocyclization of functional primary alkylamines. Treatment of primary alkylamines bearing a functional group with nitriles or their equivalents gives the corresponding heterocycles. The electrochemical oxidation of aromatic substrates in the presence of the heterocycles followed by chemical reaction under nonoxidative conditions gave the desired coupling products.
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.
Synthesis of 3-(Arylsulfonyl)benzothiophenes and Benzoselenophenes via TBHP-Initiated Radical Cyclization of 2-Alkynylthioanisoles or -selenoanisoles with Sulfinic Acids
Xu, Jian,Yu, Xiaoxia,Yan, Jianxiang,Song, Qiuling
, p. 6292 - 6295 (2017)
tert-Butyl hydroperoxide-initiated radical cyclization of 2-alkynylthioanisoles or -selenoanisoles with sulfinic acids has been developed. This reaction is applicable to a wide substrate scope via one C(sp3)-S(Se) bond cleavage and two C(sp2)-S(Se) bond formation, leading to the synthesis of 3-(arylsulfonyl)benzothiophenes or -benzoselenophenes under mild conditions.
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.
Para-coupling of phenols with C2/C3-substituted benzothiophene S-oxides
He, Zhen,Biremond, Tony,Perry, Gregory J.P.,Procter, David J.
, (2020)
C2 and C3 substituted benzothiophenes are common structures in medicinal and materials chemistry. The cross-coupling of phenols with benzothiophenes is a useful route towards these important molecules. In this report we reveal an efficient C–H/C–H-type cross-coupling of benzothiophenes, activated as their S-oxides, with phenols to give C2/C3 arylated benzothiophenes. Whereas previous reports describe cross-coupling at the ortho-position between phenols and sulfoxides, this procedure allows para-functionalization of phenols that typically have their ortho positions blocked.
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.
Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction
Hegde, Rajeev V.,Ong, Tiow-Gan,Ambre, Ram,Jadhav, Arvind H.,Patil, Siddappa A.,Dateer, Ramesh B.
, p. 1397 - 1405 (2021)
Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]
Annulative π-Extension (APEX) of Heteroarenes with Dibenzosiloles and Dibenzogermoles by Palladium/o-Chloranil Catalysis
Ozaki, Kyohei,Matsuoka, Wataru,Ito, Hideto,Itami, Kenichiro
, p. 1930 - 1933 (2017)
Annulative π-extension (APEX) reactions of heteroarenes are described herein. A catalytic system comprising a cationic palladium species and o-chloranil using dimethyldibenzosiloles as π-extending agents enabled the extension of the π-system of benzo[b]thiophenes. π-Extended dibenzofurans and carbazoles could also be obtained from benzofuran and N-tosylindole, respectively, with dimethyldibenzogermole as a germanium-based π-extending agent. Mechanistic investigations indicated two possible reaction pathways involving carbopalladation-based double C-H arylation of benzothiophene or formal cycloaddition/oxidation cascades.
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.
An efficient tandem elimination-cyclization-desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates
Chen, Wei,Li, Pinhua,Miao, Tao,Meng, Ling-Guo,Wang, Lei
, p. 420 - 424 (2013)
An efficient tandem elimination-cyclization-desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates has been developed. In the presence of TBAF-PdCl2-Cu(OAc)2-NEt 3, the reactions gen
