10273-89-9Relevant articles and documents
Manganese-catalyzed directed methylation of C(sp2)-H bonds at 25 °C with high catalytic turnover
Sato, Takenari,Yoshida, Takumi,Al Mamari, Hamad H.,Ilies, Laurean,Nakamura, Eiichi
, p. 5458 - 5461 (2017)
We report here a manganese-catalyzed C-H methylation reaction of considerable substrate scope, using MeMgBr, a catalytic amount of MnCl2· 2LiCl, and an organic dihalide oxidant. The reaction features ambient temperature, low catalyst loading, typically 1%, high catalytic turnover reaching 5.9 × 103, and no need for an extraneous ligand and illustrates a unique catalytic use of simple manganese salts for C-H activation, which so far has relied on catalysis by manganese carbonyls.
Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Aryl Chlorides
Hoshi, Takashi,Nakazawa, Taichi,Saitoh, Ippei,Mori, Ayako,Suzuki, Toshio,Sakai, Jun-Ichi,Hagiwara, Hisahiro
, p. 2063 - 2066 (2008)
High activity in the palladium-catalyzed Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for the construction of highly hindered tetra-ortho- substituted biaryls can be achieved in good to excellent yields with low catalyst loadings in short reaction times.
Catalytic meta-selective C-H functionalization to construct quaternary carbon centres
Paterson, Andrew J.,St John-Campbell, Sahra,Mahon, Mary F.,Press, Neil J.,Frost, Christopher G.
, p. 12807 - 12810 (2015)
A catalytic meta-selective C-H functionalization of 2-phenylpyridines using a range of tertiary halides is described. The protocol is simple to perform and uses commercially available reagents to construct challenging quaternary carbon centres in a regioselective manner. Preliminary studies suggest the C-H functionalization proceeds through a radical process directed via a remote σ-activation.
Cucurbit[8]uril recognition of rapidly interconverting diastereomers
Joseph, Roymon,Masson, Eric
, p. 632 - 641 (2014)
The diastereoselectivity of Cucurbit[8]uril (CB[8]) binding was probed towards a series of rapidly interconverting diastereomers containing a Caryl-Caryl chiral axis and at least one other stereocenter. Relative binding affinities of up to 4.9 were determined when CB[8] interacted with ortho, meta, ortho′-substituted biphenyls bearing a chiral dialkylsulfonium substituent at their meta-position. Diastereoselectivities of up to 2.4-fold were obtained for ortho′-substituted 2-phenylpyridinium derivatives that bear a chiral myrtenyl N-substituent prone to CB[8] binding.
Palladium (II) Complexes Containing 2-Phenylpyridine Derivatives: Synthesis, Molecular Structures, and Catalytic Activity for Suzuki–Miyaura Cross-Coupling Reactions
Adamson, A.,Alhaddad, M. R.,Arshad, M. N.,Asiri, A. M.,Budiman, Y. P.,Mkhalid, I.,Muhammad, R.
, p. 466 - 475 (2020)
The preparation and characterization of a series of new 2-phenylpyridine derivative ligands consisting of 2-(R) pyridine (R = mesityl (L1), 2,6-dimethylphenyl (L2), o-tolyl (L3), m-tolyl (L4), p-tolyl (L5), o-methoxyphenyl (L6), and p-methoxyphenyl (L7)) and their Pd complexes [PdCl2L2] (L1–L7) is investigated using a combination of X-ray diffraction spectroscopy, GC-MS, and NMR. The crystal structures show that the Pd complexes adopt a square planar geometry, and the monodentate ligand is coordinated through the N donor of the pyridine ring to the Pd atom. The catalytic activities of the synthesized complexes are investigated. The square planar Pd complex trans-[(2-mesitylpy)2PdCl2)] shows a high efficiency in promoting Suzuki-Miyaura cross coupling in an aqueous solvent under aerobic conditions.
Easily prepared air- and moisture-stable Pd-NHC (NHC = N-heterocyclic carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction
O'Brien, Christopher J.,Kantchev, Eric Assen B.,Valente, Cory,Hadei, Niloufar,Chass, Gregory A.,Lough, Alan,Hopkinson, Alan C.,Organ, Michael G.
, p. 4743 - 4748 (2006)
The synthesis of NHC-PdCl2-3-chloropyridine (NHC = N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.
Does the 2-Pyridyl Cation Behave Like an Aryne ?
Bunnett, Joseph F.,Singh, Paramjit
, p. 4567 - 4569 (1981)
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α-Halo carbonyls enable: Meta selective primary, secondary and tertiary C-H alkylations by ruthenium catalysis
Paterson, Andrew J.,Heron, Callum J.,McMullin, Claire L.,Mahon, Mary F.,Press, Neil J.,Frost, Christopher G.
, p. 5993 - 6000 (2017)
A catalytic meta selective C-H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(ii) complex activates the substrate molecule and is responsible for the meta selectivity observed. A distinct second activation of the coupling partner allows site selective reaction between both components.
Palladium-catalyzed cross-coupling of aryl halides using organotitanium nucleophiles
Lee, Hang Wai,Lam, Fuk Loi,So, Chau Ming,Lau, Chak Po,Chan, Albert S. C.,Kwong, Fuk Yee
, (2009)
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A unique six-membered chelated iridium complex
Ammermann, Sven,Daniliuc, Constantin,Jones, Peter G.,Du Mont, Wolf-Walther,Kowalsky, Wolfgang,Johannes, Hans-Hermann
, p. 4095 - 4098 (2008)
The reaction of 2-(3-methylbiphenyl-2-yl)pyridine with IrCl 3?nH2O in the presence of water incorporates a tightly bonded CO at the iridium center; in the subsequent reaction with picolinic acid a complex revealing an unusual CH activation of a methyl group is formed.
Rhodium-Catalyzed C?H Methylation and Alkylation Reactions by Carbene-Transfer Reactions
Empel, Claire,Jana, Sripati,Langletz, Tim,Koenigs, Rene M.
supporting information, (2022/02/09)
In this combined computational and experimental study, the C?H functionalization of 2-phenyl pyridine with diazoalkanes was investigated. Initial evaluation by computational methods allowed the evaluation of different metal catalysts and diazoalkanes and their compatibility in this C?H functionalization reaction. With these findings, suitable reaction conditions for the C?H methylation reactions were quickly identified by using highly reactive TMS diazomethane and C?H alkylation reactions with donor/acceptor diazoalkanes, which is applied to a broad scope on alkylation reactions of 2-aryl pyridines with TMS diazomethane and donor/acceptor diazoalkane (51 examples, up to 98 % yield).
Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki-Miyaura cross-coupling reactions
Holzapfel, Cedric W.,Lamola, Jairus L.,Maumela, Munaka Christopher,Moshapo, Paseka T.
, p. 26883 - 26891 (2021/08/17)
A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks is described. The rigid biaryl phosphacycles are efficient for Suzuki-Miyaura cross-coupling of aryl bromides and chlorides. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature.
