2018
DOI: 10.1039/c8ra04094j
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An efficient class of bis-NHC salts: applications in Pd-catalyzed reactions under mild reaction conditions

Abstract: This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials.

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Cited by 22 publications
(15 citation statements)
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“…The fact is that even the coupling of 2‐bromo‐ N , N ‐dimethylaniline with phenylboronic acid is accompanied by a hydrodehalogenation process, which in some cases may become predominant . Only the use of specific catalysts and N ‐heterocyclic carbene ligands can overcome this difficulty. Another problem that arises during the reaction of sterically hindered coupling partners is hydrodeboronation .…”
Section: Resultsmentioning
confidence: 98%
“…The fact is that even the coupling of 2‐bromo‐ N , N ‐dimethylaniline with phenylboronic acid is accompanied by a hydrodehalogenation process, which in some cases may become predominant . Only the use of specific catalysts and N ‐heterocyclic carbene ligands can overcome this difficulty. Another problem that arises during the reaction of sterically hindered coupling partners is hydrodeboronation .…”
Section: Resultsmentioning
confidence: 98%
“…High-resolution mass spectra were obtained with a Finnigan/Thermo Quest MAT 95XL mass spectrometer using either the electron impact (EI) or the electrospray ionization (ESI) method. The synthesis of the bis-NHC-Ag complex was carried out according to our previous report [50].…”
Section: General Methodsmentioning
confidence: 99%
“…The NHC-ligated Pd NPs present an efficient catalytic activity in the catalysis [44][45][46][47][48]. We recently reported an in situ-generated bis-NHC/Pd(OAc)2 catalytic system, which was derived from bis-benzimidazolium salt and Pd(OAc)2, as a catalyst for the Suzuki-Miyaura reaction, Mizoroki-Heck reaction, and Friedel-Crafts alkylation reaction of indole and nitrostyrene in good to excellent yields (Figure 1a) [49,50]. Motivated by these results we continued our efforts to develop an efficient bis-NHC-Ag/Pd(OAc)2 catalytic system to catalyze chemoselective transfer hydrogenation with TEAF as a hydrogen donor (Figure 1b).…”
Section: Introductionmentioning
confidence: 99%
“…[34] Treatment of 15 with iso-amyl nitrite in the presence of acetic acid gave the corresponding bicyclic benzotriazole 16, [35] whereas heating the same diamine in formic acid along with triethyl orthoformate at 120 °C (in a sealed tube) afforded benzimidazole 17. [36] All ester intermediates (11, 13, 16 and 17) were subjected to hydrolysis, followed by coupling of the resulting carboxylic acids with isoindoline in the presence of HATU and DIPEA to afford the desired amides (Table 1). Cleavage of the methyl ethers gave the corresponding phenols 18, 19, 20, and 21, respectively.…”
Section: Chemistrymentioning
confidence: 99%