13629-73-7Relevant academic research and scientific papers
Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
Wu, Qingsong,Han, Shuaijun,Ren, Xiaoxiao,Lu, Hongtao,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 6345 - 6348 (2018/10/20)
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
Pd-PEPPSI-IHeptCl: A General-Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs
Atwater, Bruce,Chandrasoma, Nalin,Mitchell, David,Rodriguez, Michael J.,Organ, Michael G.
supporting information, p. 14531 - 14534 (2016/10/03)
Dichloro[1,3-bis(2,6-di-4-heptylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (Pd-PEPPSI-IHeptCl), a new, very bulky yet flexible Pd–N-heterocyclic carbene (NHC) complex has been evaluated in the cross-coupling of secondary alkylzinc
Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
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Paragraph 1131; 1132, (2015/08/04)
The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.
NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
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Page/Page column 139; 140, (2015/09/23)
The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.
Methylation of phenol and its derivatives with dimethyl carbonate in the presence of Mn2(CO)10, W(CO)6, and Co2(CO)8
Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.
, p. 330 - 334 (2015/05/04)
Aryl methyl ethers were synthesized by reactions of phenol, substituted phenols, and α- and β-naphthols with dimethyl carbonate in the presence of manganese, tungsten, and cobalt carbonyls. Optimal reactant and catalyst ratios and reaction conditions were found to ensure selective formation of aryl methyl ethers.
Pd-PEPPSI-IPentCl: A highly effective catalyst for the selective cross-coupling of secondary organozinc reagents
Pompeo, Matthew,Hadei, Niloufar,Organ, Michael G.,Froese, Robert D. J.
supporting information, p. 11354 - 11357,4 (2012/12/12)
No migration? No problem. A series of new N-heterocyclic carbene based Pd complexes has been created and evaluated in the Negishi cross-coupling of aryl and heteroaryl chlorides, bromides, and triflates with a variety of secondary alkylzinc reagents (see scheme). The direct elimination product is nearly exclusively formed; in most examples there is no migratory insertion at all. Copyright
Pd-PEPPSI-IPentCl: A highly effective catalyst for the selective cross-coupling of secondary organozinc reagents
Pompeo, Matthew,Froese, Robert D. J.,Hadei, Niloufar,Organ, Michael G.
supporting information, p. 11354 - 11357 (2013/01/15)
No migration? No problem! A series of new N-heterocyclic carbene based Pd complexes has been created and evaluated in the Negishi cross-coupling of aryl and heteroaryl chlorides, bromides, and triflates with a variety of secondary alkylzinc reagents (see scheme). The direct elimination product is nearly exclusively formed; in most examples there is no migratory insertion at all. Copyright
A 'meta effect' in the fragmentation reactions of ionised alkyl phenols and alkyl anisoles
Bouchoux, Guy,Sablier, Michel,Miyakoshi, Tetsuo,Honda, Takashi
scheme or table, p. 539 - 546 (2012/09/22)
The competition between benzylic cleavage (simple bond fission [SBF]) and retro-ene rearrangement (RER) from ionised ortho, meta and para RC 6H4OH and RC6H4OCH3 (R = n-C3H7, n-C4H9, n-C5H11, n-C7H15, n-C9H19, n-C 15H31) is examined. It is observed that the SBF/RER ratio is significantly influenced by the position of the substituent on the aromatic ring. As a rule, phenols and anisoles substituted by an alkyl group in meta position lead to more abundant methylene-2,4-cyclohexadiene cations (RER fragmentation) than their ortho and para homologues. This 'meta effect' is explained on the basis of energetic and kinetic of the two reaction channels. Quantum chemistry computations have been used to provide estimate of the thermochemistry associated with these two fragmentation routes. G3B3 calculation shows that a hydroxy or a methoxy group in the meta position destabilises the SBF and stabilises the RER product ions. Modelling of the SBF/RER intensities ratio has been performed assuming two single reaction rates for both fragmentation processes and computing them within the statistical RRKM formalism in the case of ortho, meta and para butyl phenols. It is clearly demonstrated that, combining thermochemistry and kinetics, the inequality (SBF/RER) metaorthopara holds for the butyl phenols series. It is expected that the 'meta effect' described in this study enables unequivocal identification of meta isomers from ortho and para isomers not only of alkyl phenols and alkyl anisoles but also in other alkyl benzene series. Copyright
Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent
Alimsiz, Seluk,Organ, Michael G.
supporting information; experimental part, p. 5181 - 5183 (2011/06/09)
Pd-PEPPSI-IPent has proven to be an excellent catalyst for the Negishi cross-coupling reaction of secondary alkylzinc reagents with a wide variety of aryl/heteroaryl halides. Importantly, β-hydride elimination/migratory insertion of the organometallic leading to the production of isomeric coupling products has been significantly reduced using the highly-hindered Ipent ligand.
Cross-coupling reactions through the intramolecular activation of Alkyl(triorgano)silanes
Nakao, Yoshiaki,Takeda, Masahide,Matsumoto, Takuya,Hiyama, Tamejiro
supporting information; scheme or table, p. 4447 - 4450 (2010/08/19)
(Figure Presented) Cross-Si-ing the Jordan: Cross-coupling reactions of 2-(2-hydroxyprop-2-yl)phenylsubstituted alkylsilanes with a variety of aryl halides proceed in the presence of palladium and copper catalysts. The use of K3PO4 base allows for highly chemoselective alkyl coupling with both primary and secondary alkyl groups (Alk).
