27331-43-7Relevant articles and documents
C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex
Tang, Huiling,Liu, Mengna,Zhu, Meiqi,Cui, Benqiang,Shi, Yanhui,Cao, Changsheng
, (2021/09/15)
We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.
Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles
Russell, John E. A.,Entz, Emily D.,Joyce, Ian M.,Neufeldt, Sharon R.
, p. 3304 - 3310 (2019/03/26)
Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl - heteroaryl, aryl - alkenyl, and aryl - alkynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II) - chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.
Palladium nanoparticles stabilized by phosphine ligand for aqueous phase room temperature suzuki-Miyaura coupling
Ge, Jiyuan,Jiang, Jian,Yuan, Chenhuan,Zhang, Chaozhi,Liu, Minghua
supporting information, p. 1142 - 1145 (2017/03/02)
Water soluble phosphine ligand triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt (TPPTS) was used as the stabilizer as well as the activator to the palladium nanoparticles, which showed a high catalytic performance for aqueous phase Suzuki-Miyaura coupling reaction at room temperature.
[4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity
Novikov, Roman A.,Tarasova, Anna V.,Denisov, Dmitry A.,Borisov, Denis D.,Korolev, Victor A.,Timofeev, Vladimir P.,Tomilov, Yury V.
, p. 2724 - 2738 (2017/03/14)
A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.
Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents
Heijnen, Dorus,Tosi, Filippo,Vila, Carlos,Stuart, Marc C. A.,Elsinga, Philip H.,Szymanski, Wiktor,Feringa, Ben L.
supporting information, p. 3354 - 3359 (2017/03/17)
The discovery of an ultrafast cross-coupling of alkyl- and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [11C]-labeled PET tracer celecoxib.
Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates
Melvin, Patrick R.,Hazari, Nilay,Beromi, Megan Mohadjer,Shah, Hemali P.,Williams, Michael J.
supporting information, p. 5784 - 5787 (2016/11/29)
Using a recently discovered precatalyst, the first Pd-catalyzed Suzuki-Miyaura reactions using aryl sulfamates that occur at room temperature are reported. In complementary work, it is demonstrated that a related precatalyst can facilitate the coupling of aryl silanolates, which are less toxic and reactive nucleophiles than boronic acids with aryl chlorides. By combining our results using modern electrophiles and nucleophiles, the first Hiyama-Denmark reactions using aryl sulfamates are reported.
TBuLi-Mediated One-Pot Direct Highly Selective Cross-Coupling of Two Distinct Aryl Bromides
Vila, Carlos,Cembellín, Sara,Hornillos, Valentín,Giannerini, Massimo,Fa?anás-Mastral, Martín,Feringa, Ben L.
supporting information, p. 15520 - 15524 (2015/11/03)
A Pd-catalyzed direct cross-coupling of two distinct aryl bromides mediated by tBuLi is described. The use of [Pd-PEPPSI-IPr] or [Pd-PEPPSI-IPent] as catalyst allows for the efficient one-pot synthesis of unsymmetrical biaryls at room temperature. The key for this selective cross-coupling is the use of an ortho-substituted bromide that undergoes lithium-halogen exchange preferentially. Bro to Bro: A palladium-catalyzed direct cross-coupling of two distinct aryl bromides mediated by tBuLi is described. The use of [Pd-PEPPSI-IPr] or [Pd-PEPPSI-IPent] as catalyst allows for the efficient one-pot synthesis of unsymmetrical biaryls at room temperature. The key for this selective cross-coupling is the use of an ortho-substituted bromide that undergoes lithium-halogen exchange preferentially.
Synthesis of palladium-bidentate complex and its application in Sonogashira and Suzuki coupling reactions
Haddad, Boumediene,Villemin, Didier,Belarbi, El-Habib
, p. 656 - 661 (2014/05/06)
A new palladium-bidentate complex [m-C6H4(CH 2ImMe)2(PdCl2)] (III) was prepared in two steps. In the first step, [m-C6H4(CH2ImMeAgCl) 2] (II) (Im = imidazole moiety) was obtained by reacting imidazolium salt [m-C6H4(CH2ImMe)2]Cl 2 (I) (prepared by quaternisation of Nmethylimidazole with 1,3-bis(chloromethyl)benzene) and Ag2O in CH2Cl 2. In the next step, treatment of (II) with Pd(CH3CN) 2Cl2 afforded complex III which was evaluated for its catalytic activity for C-C bond-formation reactions by examining the coupling reaction of 3-iodoanisole with phenylacetylene in the Sonogashira reaction. In addition, 3-methoxybiphenyls were obtained with good to excellent yields by Suzuki coupling reactions of 3-iodoanisole with phenylboronic acids or phenylborates salts in the presence of this complex.
Sustainable H2O/ethyl lactate system for ligand-free Suzuki-Miyaura reaction
Wan, Jie-Ping,Wang, Chunping,Zhou, Rihui,Liu, Yunyun
, p. 8789 - 8792 (2015/01/30)
A sustainable catalyst system consisted of H2O/ethyl lactate (EL), Pd(OAc)2 and K2CO3 has been developed as a generally applicable protocol for Suzuki-Miyaura reactions using various aryl bromides and iodides to incorporate arylboronic acids under ligand-free conditions. This protocol is advantageous owing to the employment of water and non-toxic, biomass available ethyl lactate as green media. In addition, as a co-solvent with water, ethyl lactate displayed evident superiority over conventional polar organic solvents such as DMF, DMSO and dioxane etc., which implied the additional potential function of EL as a ligand in these reactions.
Aminoborylation/Suzuki-Miyaura tandem cross coupling of aryl iodides as efficient and selective synthesis of unsymmetrical biaryls
Marciasini, Ludovic,Richy, Nicolas,Vaultier, Michel,Pucheault, Mathieu
supporting information; experimental part, p. 1553 - 1555 (2012/02/16)
Sequential borylation of a first aryl iodide using a dialkylaminoborane followed by a Suzuki-Miyaura cross coupling of second aryl iodide ended up with an efficient, selective and practical synthesis of unsymmetrical biaryls. This tandem coupling shows a wide range of applicability.
