General and highly efficient fluorinated-N-heterocyclic carbene–based catalysts for the palladium-catalyzed Suzuki–Miyaura reaction

Liu, Taoping; Zhao, Xiaoming; Shen, Qilong; Lü, Long

doi:10.1016/j.tet.2012.05.068

Cited by 30 publications

(14 citation statements)

References 56 publications

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“…Since then, there have been a few independent reports on successful Suzuki-Miyaura coupling of H-and F-BTC dihalogenides in low to good yields (38-81 %). [27] In 2009 Hermes et al reported the Suzuki-Miyaura coupling reaction of dichloride 1 and aromatic boronic acids/esters with high yields ( Table 5). [9a] During our work we were unable to reproduce the same yields starting from dichloride 1.…”

Section: Derivatisation Of the Bisthienylcyclopentenyl Corementioning

confidence: 99%

Synthesis of Symmetrical and Nonsymmetrical Bisthienylcyclopentenes

Szalóki

Pozzo

2013

Chemistry A European J

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Diarylethenes possess unique structural properties, which enabled them to find widespread applications in the field of photochromism. Nowadays, bisthienylcyclopentenes (BTCs) present the most popular subfamily of these compounds, which are widely used as P-type chromophores. This minireview summarises the main strategies for the synthesis of symmetrical and nonsymmetrical BTCs. In addition, attention is drawn to desymmetrisations achieved by monosubstitutions, which is not frequently utilised, although it can be highly advantageous. This is supported with some of the authors' latest results.

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Section: Derivatisation Of the Bisthienylcyclopentenyl Corementioning

confidence: 99%

Synthesis of Symmetrical and Nonsymmetrical Bisthienylcyclopentenes

Szalóki

Pozzo

2013

Chemistry A European J

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“…The reaction was monitored by TLC. 1 [30,31] [29] White solid. The resulting organic solution was dried with MgSO 4 and concentrated with a rotary evaporator.…”

Section: General Procedures For Suzuki-miyaura Cross-coupling Reactionsmentioning

confidence: 99%

“…The crude product was purified by preparative TLC (0.5 mm). 1 [30,32,37] 4-Acetyl-(4Ј-methyl)biphenyl: [38] White solid. The products were identified by IR and NMR ( 1 H and 13 C) spectroscopy based on the literature data.…”

Section: General Procedures For Suzuki-miyaura Cross-coupling Reactionsmentioning

confidence: 99%

C,N‐Palladacycles Containing N‐Heterocyclic Carbene and Azido Ligands – Effective Catalysts for Suzuki–Miyaura Cross‐Coupling Reactions

et al. 2012

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Azido-palladacycles containing C,N-donor and N-heterocyclic carbene ligands, [(C,N-L)Pd(N 3 )(NHC)] [NHC = IPr; 1,3bis(2,6-diisopropylphenyl)imidazol-2-ylidene], were prepared from (i) IPr and dinuclear Pd II azides, [Pd(μ-N 3 )(C,N-L n )] 2 [C,N-L 1 H = N,NЈ-dimethylbenzylamine; C,N-L 2 H = 2-(2Ј-thienyl)pyridine; C,N-L 3 H = azobenzene; C,N-L 4 H = 2-(ptolyl)pyridine], or from (ii) NaN 3 and mononuclear Pd II chloride, [Pd(Cl)(IPr)(C,N-L n )], in aqueous solution. The structures [a]

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“…However, the cost of aryl bromides is much higher than that of aryl chlorides, and so it is very impracticable to use aryl bromides in industry. N-heterocyclic carbenes (NHCs) [23][24][25][26][27][28][29] and metallocycle scaffolds have been used as alternatives to tertiary phosphines in cross-coupling reactions. And highly active catalyst systems of palladium supported by bulky electron-rich phosphines [16][17][18][19][20][21] or sterically demanding ligands are attracting much attention.…”

Section: Introductionmentioning

confidence: 99%