17171-17-4Relevant articles and documents
Iridium-catalyzed ortho-arylation of benzoic acids with arenediazonium salts
Huang, Liangbin,Hackenberger, Dagmar,Goossen, Lukas J.
, p. 12607 - 12611 (2015)
In the presence of catalytic [{IrCpCl2}2] and Ag2CO3, Li2CO3 as the base, and acetone as the solvent, benzoic acids react with arenediazonium salts to give the corresponding diaryl-2-carboxylates under mild conditions. This C-H arylation process is generally applicable to diversely substituted substrates, ranging from extremely electron-rich to electron-poor derivatives. The carboxylate directing group is widely available and can be removed tracelessly or employed for further derivatization. Orthogonality to halide-based cross-couplings is achieved by the use of diazonium salts, which can be coupled even in the presence of iodo substituents. Directing rather than removed: In the presence of catalytic [{IrCpCl2}2], benzoic acids react with arenediazonium salts to give the corresponding diaryl-2-carboxylates. If desired, the carboxylate directing group can be removed by in situ protodecarboxylation.
Palladium-catalyzed direct C-H arylation of unactivated arenes with aryl Halides
Hong, Wenkun,Qiu, Yatao,Yao, Zhiyi,Wang, Zhaoyang,Jiang, Sheng
, p. 4916 - 4919 (2011)
An efficient palladium-catalyzed direct C-H arylation of unactivated arenes has been discovered. This method employs aryl halides as the direct coupling partners with arenes without using any external ligands. This catalysis opens a new methodology for the preparation of symmetrical as well as unsymmetrical biaryls in a user-friendly approach.
Efficient Suzuki reaction catalyzed by recyclable clay carbapalladacycle nanocomposite in ionic liquid media
Kaur, Amanpreet,Singh, Vasundhara
, p. 1128 - 1131 (2015)
In this Letter, we report the efficient recyclability and recoverability of ionic tagged carbapalladacycle and its hybrid MMT clay-nanocomposite catalyst in ionic liquid media [TMBA]NTf2 for the Suzuki reaction. It has several distinct advantages which include the use of low levels of catalyst concentration, formation of desired products in high yields and good selectivity using chloro, bromo and iodo substituted aryl halides, and negligible formation of homo coupling products.
Scope of the desulfinylative palladium-catalyzed cross-coupling of aryl sulfinates with aryl bromides
Ortgies, Dirk H.,Barthelme, Alexandre,Aly, Sara,Desharnais, Brigitte,Rioux, Steven,Forgione, Pat
, p. 694 - 702 (2013)
Herein is described the full scope of a desulfinylative cross-coupling of aryl sulfinates with aryl bromides. Optimized conditions were established and a bidentate phosphine ligand was found to be the key in obtaining good cross-coupling yields. Preliminary efforts to elucidate the reaction mechanism suggest that a Pd(0)-catalyzed mechanism is operative. Georg Thieme Verlag Stuttgart · New York.
An efficient protocol for a Pd(OAc)2-catalyzed ligand-free Suzuki reaction in toluene
Liu, Ning,Liu, Chun,Jin, Zilin
, p. 1316 - 1320 (2010)
An efficient protocol for a Pd(OAc)2-catalyzed ligand-free Suzuki reaction of aryl bromides with arylboronic acids in the presence of K3PO4·7H2O in toluene under mild and aerobic conditions afforded cross-coupling products in good to excellent yields. Under the optimized reaction conditions (i.e., 0.5 mmol ArBr, 0.75 mmol ArB(OH)2, 1 mol Pd(OAc)2, 1.0 mmol K3PO 4·7H2O, 2 ml toluene), the Suzuki reaction between 4-nitrobromobenzene and phenylboronic acid afforded a 99 isolated yield in 5 min at 75 °C and a TOF of up to 1 188 h-1.
Palladium nanoparticles supported on cucurbit [6]uril: An efficient heterogeneous catalyst for the Suzuki reaction under mild conditions
Karami,Haghighat Naeini
, p. 33 - 39 (2015)
A new NC palladacycle was synthesized and supported on cucurbit[6]uril (CB[6]). The CB[6]-supported palladium was used as an efficient nanocatalyst for the Suzuki reaction. In these reactions various aryl halides were reacted with arylboronic acids in H2O-EtOH at both room temperature and 40°C. The obtained Pd nanocatalyst exhibited excellent reactivity and stability in C-C bond formation, which confirms that the catalyst is a completely active heterogeneous species. The Pd nanocatalyst was characterized using X-ray diffraction, scanning electron microscopy and transmission electron microscopy.
Porous single-crystalline palladium nanoparticles with high catalytic activities
Wang, Feng,Li, Chuanhao,Sun, Ling-Dong,Xu, Chun-Hu,Wang, Jianfang,Yu, Jimmy C.,Yan, Chun-Hua
, p. 4872 - 4876 (2012)
Palladium's pore cousin: A facile approach is described for the size-controlled preparation of porous single-crystalline Pd nanoparticles. These porous Pd nanoparticles exhibit size-independent catalytic activities for the Suzuki coupling and are more active than commercial Pd/C catalysts. Copyright
Simple alcohols promoted direct C-H arylation of unactivated arenes with aryl halides
Liu, Wei,Tian, Fei,Wang, Xiaolei,Yu, Hao,Bi, Yanlan
, p. 2983 - 2985 (2013)
Simple and cheap alcohols can promote the direct arylation of unactivated arenes with aryl iodides and bromides in the presence of potassium tert-butoxide. This transition-metal-free aromatic C-H transformation offers a cheap and easy practical way to synthesize biaryls under mild conditions. The Royal Society of Chemistry.
Direct arylation of unactivated aromatic C-H bonds catalyzed by a stable organic radical
Yong, Guo-Ping,She, Wen-Long,Zhang, Yi-Man,Li, Ying-Zhou
, p. 11766 - 11768 (2011)
A stable zwitterionic radical can catalyze direct arylation of unactivated aromatic C-H bonds via a chain homolytic aromatic substitution mechanism in the presence of potassium tert-butoxide.
Graphene oxide-palladium modified Ag-AgBr: A visible-light-responsive photocatalyst for the Suzuki coupling reaction
Gao, Shutao,Shang, Ningzhao,Feng, Cheng,Wang, Chun,Wang, Zhi
, p. 39242 - 39247 (2014)
The efficient utilization of the abundant and economical solar energy has received tremendous attention due to increased environmental and energy concerns. In this report, a plasmonic Ag-AgBr photocatalyst functionalized with graphene oxide-Pd was successfully fabricated and used as an efficient visible-light-responsive photocatalyst for the Suzuki coupling reaction. The integration of plasmonic Ag-AgBr with Pd nanoparticles supported on graphene oxide enabled efficient visible light harvesting for the catalytic reaction on the heterojunction structure. A possible catalytic mechanism for the highly efficient photocatalyst is proposed. This work provides a convenient means for the design of efficient catalysts that are composed of a photocatalyst and a catalytically active transition metal for various organic transformations driven by visible light.
