Reductive amination with 5-ethyl-2-methylpyridine borane

Burkhardt, Elizabeth R.; Coleridge, Brian M.

doi:10.1016/j.tetlet.2008.06.095

Cited by 54 publications

(28 citation statements)

References 16 publications

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“…In order to carry out a direct reductive amination successfully, the choice of the reducing agent is critical. The most commonly used processes and reagents are: catalytic hydrogenation, borohydrides, 4 and amine boranes 5 to name but a few, but even water-soluble iron complexes have emerged very recently as catalysts. 6 As a further possibility to broaden the scope of the methodology, these reaction conditions make it possible to carry out simultaneous reduction of other functional groups present in the starting carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

An improved method for the synthesis of 2-, 3- and 4-dialkylaminomethylanilines

Pete¹,

Szántay²

2009

Arkivoc

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Section: Introductionmentioning

confidence: 99%

An improved method for the synthesis of 2-, 3- and 4-dialkylaminomethylanilines

Pete¹,

Szántay²

2009

Arkivoc

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“…Then, compound 3 was condensed with potassium 4-formylphenyltrifluoroborate to give the corresponding imine intermediate. Finally, the resulting intermediate was directly reduced by 5-ethyl-2-methylpyridine borane complex (PEMB) [13] to give the final product 4 in 64% yield. …”

Section: Resultsmentioning

confidence: 99%

Potassium {4-[(3S,6S,9S)-3,6-dibenzyl-9-isopropyl-4,7,10-trioxo-11–oxa-2,5,8-triazadodecyl]phenyl}trifluoroborate

Tsai

Lin

Hsieh

et al. 2014

Molbank

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[5,6], and oxazaborolidines [7,8] are frequently used boron functional groups. Having an empty p-orbital on the trivalent boron atom, these analogs interact with their targets to form tetrahedral intermediates. Organotrifluoroborates, on the other hand, are seldom considered in biological applications due to their lack of an empty p-orbital. Srebnik and coworkers, the first group to investigate the biological activity of a series of aryl organotrifluoroborates in enzyme-inhibition assays, reported that aryl potassium trifluoroborates were much more potent than the corresponding boronic acids against α-chymotrypsin and trypsin [9,10]. The toxicological profile of organotrifluoroborates were also investigated by Oliveira and co-workers, who showed that thiophene-3-trifluoroborate exhibits minimal toxicity in a mouse model, and concluded that this class of compounds is suitable for further development as pharmacologically active agents [11]. Despite their promising biological studies, the reported studies of organotrifluoroborates OPEN ACCESS

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“…There are several reagents and catalysts reported in the literature for reductive amination, following direct as well as indirect approaches [14][15][16][17]. In most of these methods are used acid catalyst/reagent along with a reducing agent like NaBH 4 .…”

Section: Introductionmentioning

confidence: 99%

“…However, reported conversions are low and require long reaction time and high temperature. Though many of the reported protocols for reductive amination reaction work well for the preparation of tertiary amines and synthesis of secondary amines is compromised by over alkylation in many cases [7,[14][15][16][17]. Thus, it is necessary to develop an alternative method that employs simple and environmentally benign conditions for all three types of amines.…”

Section: Introductionmentioning

confidence: 99%

Reductive Amination of Carbonyl Compounds over Silica Supported Palladium Exchanged Molybdophosphoric Acid Catalysts

2012

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Palladium exchanged molybdophosphoric acid supported on silica is reported as a highly effective catalyst for direct reductive amination of carbonyl compounds. The catalysts are characterized by X-ray diffraction and FT-infrared spectroscopy. The characterization results support the existence of Keggin ion of heteropoly molybdate on silica. The catalyst is facile, water tolerable and environmentally benign for reductive amination. A variety of secondary and tertiary amines can be synthesized over this catalyst in excellent yields under mild reaction conditions. A plausible reaction mechanism is proposed for the reductive amination of carbonyl compounds over this catalyst.

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Reductive amination with 5-ethyl-2-methylpyridine borane

Cited by 54 publications

References 16 publications

An improved method for the synthesis of 2-, 3- and 4-dialkylaminomethylanilines

An improved method for the synthesis of 2-, 3- and 4-dialkylaminomethylanilines

Potassium {4-[(3S,6S,9S)-3,6-dibenzyl-9-isopropyl-4,7,10-trioxo-11–oxa-2,5,8-triazadodecyl]phenyl}trifluoroborate

Reductive Amination of Carbonyl Compounds over Silica Supported Palladium Exchanged Molybdophosphoric Acid Catalysts

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