613-42-3Relevant articles and documents
Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction
Boukherroub, Rabah,Mirza-Aghayan, Maryam,Mohammadi, Marzieh
, (2021/11/22)
Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.
Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides
Chan, Cheng-Lin,Hsu, Che-Ming,Lee, Shao-Chi,Li, Li-Yun,Liao, Hsuan-Hung,Mi?oza, Shinje,Tsai, Hao-En,Tsai, Zong-Nan,Tsao, Yong-Ting
, (2022/02/07)
The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.
Photocatalytic Dehydroxymethylative Arylation by Synergistic Cerium and Nickel Catalysis
Chen, Yuegang,Wang, Xin,He, Xu,An, Qing,Zuo, Zhiwei
supporting information, p. 4896 - 4902 (2021/05/04)
Under mild reaction conditions with inexpensive cerium and nickel catalysts, easily accessible free alcohols can now be utilized as operationally simple and robust carbon pronucleophiles in selective C(sp3)-C(sp2) cross-couplings. Facilitated by automated high-throughput experimentation, sterically encumbered benzoate ligands have been identified for robust cerium complexes, enabling the synergistic cooperation of cerium catalysis in the emerging metallaphotoredox catalysis. A broad range of free alcohols and aromatic halides can be facilely employed in this transformation, representing a new paradigm for the C(sp3)-C(sp2) bond construction between free alcohols and aryl halides with the extrusion of formaldehyde. Moreover, mechanistic investigations have been conducted, leading to the identification of a tribenzoate cerium(III) complex as a viable intermediate.
