2009
DOI: 10.1002/adsc.200900323
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Aminations of Aryl Bromides in Water at Room Temperature

Abstract: Unsymmetrical di-and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium. Keywords aminations; amphiphiles; micellar catalysis; surfactantsThe direct amination of aromatic rings via palladium-catalyzed processes could be considered among the most important of the advances in synthesis within the past two decades. A wide range of C-N bond-forming reactions are available;… Show more

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Cited by 81 publications
(57 citation statements)
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“…As described in previous publications, the use of more lipophilic bases like TIPSOH/KOH and TMSOK may be beneficial for micellar catalysis due to better penetration of such based into the inner core of a micelle. 15 However for this particular reaction, the influence of the base was minimal and comparable yields using four different bases were observed (Table 3), which would be in agreement with an (at least partly) interfacial mechanism. Using the now optimized conditions, a series of functionalized 4-dihydroquinolinones were isolated in good to excellent yields using differently substituted α,β-unsaturated esters (see Table 4).…”
Section: Resultssupporting
confidence: 81%
“…As described in previous publications, the use of more lipophilic bases like TIPSOH/KOH and TMSOK may be beneficial for micellar catalysis due to better penetration of such based into the inner core of a micelle. 15 However for this particular reaction, the influence of the base was minimal and comparable yields using four different bases were observed (Table 3), which would be in agreement with an (at least partly) interfacial mechanism. Using the now optimized conditions, a series of functionalized 4-dihydroquinolinones were isolated in good to excellent yields using differently substituted α,β-unsaturated esters (see Table 4).…”
Section: Resultssupporting
confidence: 81%
“…1 H NMR (400 MHz, CDCl 3 ) δ 7.94–7.89 (d, J = 9.0 Hz, 1H), 7.89–7.84 (d, J = 8.3 Hz, 1H), 7.84–7.80 (d, J = 8.1 Hz, 1H), 7.69–7.64 (t, J = 1.5 Hz, 1H), 7.48–7.42 (td, J = 6.8, 1.5 Hz, 1H), 7.40–7.33 (td, J = 6.8, 1.2 Hz, 2H), 6.65–6.62 (d, J = 1.5 Hz, 2H), 3.94 (s, 3H). 24 …”
Section: Methodsmentioning
confidence: 99%
“…14 The newly introduced, less expensive second-generation surfactant TPGS-750-M (Fig. 1), 15a which varies from PTS in its four carbon succinate linker and contains MPEG-750 instead of PEG-600, was selected as the enabling technology for this study in water.…”
Section: Resultsmentioning
confidence: 99%
“…14 Thus, alkoxide bases that are branched at carbon bearing oxygen afforded good results, such as tert -butoxide and triisopropylsilyloxide. Presumably this structural array decreases ionic character while increasing lipophilicity and solubility within the lipophilic core of TPGS-750-M nanomicelles, leading to smooth and complete reactions.…”
Section: Resultsmentioning
confidence: 99%