20442-73-3Relevant academic research and scientific papers
Molybdenum(II)-catalyzed alkylation of electron-rich aromatics with allylic acetates
Malkov, Andrei V.,Davis, Stuart L.,Mitchell, William L.,Kocovsky, Pavel
, p. 4899 - 4902 (1997)
The molybdenum(II) complex [Mo(CO)4Br2]2 has been found to catalyze allylic substitution with aromatic ethers, e.g., anisole (7), as nucleophiles. The reaction is remarkably para-selective (e.g. 7 + 8 → 11).
Preparation of 1,3-Diarylpropenes by Phosphine-Free Palladium(0)-Catalyzed Suzuki-Type Coupling of Allyl Bromides with Arylboronic Acids
Moreno-Manas, Marcial,Pajuelo, Francesca,Pleixats, Roser
, p. 2396 - 2397 (1995)
1,2-Diarylpropenes 3 featuring different substituents at the aryl rings are obtained in high yields by a modified Suzuki coupling between cinnamyl bromides and arylboronic acids using the phosphine-free Pd(dba)n (n = 1.5-2) as catalyst, in benzene and in
A macrocyclic triolefinic palladium(0) complex covalently anchored to a mesostructured silica as active and reusable catalyst for Suzuki cross-coupling reactions
Blanco, Belén,Mehdi, Ahmad,Moreno-Ma?as, Marcial,Pleixats, Roser,Reyé, Catherine
, p. 8789 - 8791 (2004)
A mesostructured hybrid material containing a 15-membered triazamacrocyclic triolefinic palladium(0) complex was prepared and tested as a reusable heterogeneous catalyst for Suzuki cross-couplings in organic solvents. A mesoporous hybrid material containi
Bimetallic nano alloy architecture on a special polymer: Ni or Cu merged with Pd for the promotion of the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling
Patil, Vijay P,Kashid, Abhijit A,Solanki, Bhanupratap S,Kharul, Ulhas K,Iyer, Suresh
, (2021/02/12)
Abstract: Novel Ni-Pd and Cu-Pd bimetallic nano alloys was designed and heterogenized on the highly robust ABPBI [poly(2,5-benzimidazole)] polymer in high yields using NaBH4 as reducing agent. These were versatile ligand free catalysts for the Mizoroki–Heck reaction and Suzuki–Miyaura coupling. The bimetallic Ni-Pd-ABPBI catalyst for the Mizoroki–Heck reaction of 4-iodo anisole could be recycled 5 times with high yields. Aryl bromides could also be activated for the Mizoroki–Heck reaction using Cu-Pd-ABPBI NP catalysts, with moderate yields. Graphic abstract: Synopsis Novel bimetallic Ni-Pd and Cu-Pd nano alloys, heterogenized on the robust ABPBI [poly(2,5-benzimidazole)] polymer using NaBH4 as reducing agent, is described. These were versatile ligand free, noble metal conservative catalysts, for the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling. Aryl bromides were activated for the Mizoroki–Heck reaction using the Cu-Pd-ABPBI catalyst.[Figure not available: see fulltext.]
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
Yu, Hang,Wang, Zhong-Xia
, p. 9723 - 9731 (2021/12/01)
Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols proceeds readily under mild conditions in the presence of zinc powder and MgCl2to produce allylarenes in 25-92% yields. The reaction shows high regioselectivit
Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
Luo, Jian,Hu, Bo,Wu, Wenda,Hu, Maowei,Liu, T. Leo
, p. 6107 - 6116 (2021/02/01)
Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.
Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids
Pal, Suman,Cotard, Marine,Gérardin, Baptiste,Hoarau, Christophe,Schneider, Cédric
supporting information, p. 3130 - 3135 (2021/05/05)
Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.
In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids
Wang, Yu-Bin,Liu, Bin-Yuan,Bu, Qingqing,Dai, Bin,Liu, Ning
, p. 2930 - 2940 (2020/06/17)
A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).
Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon
Horino, Yoshikazu,Ishibashi, Mayo,Nakasai, Kosuke,Korenaga, Toshinobu
, (2020/08/28)
The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.
Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation
Zhang, Yu-Lan,Yang, Lei,Wu, Jie,Zhu, Chunyin,Wang, Peng
, p. 7768 - 7772 (2020/10/09)
Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl rad
