Nickel-aluminum alloy as a reducing agent

Keefer, Larry K.; Lunn, George

doi:10.1021/cr00093a002

Cited by 68 publications

(22 citation statements)

References 17 publications

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“…In conformity with the works reported in references [19,20] and considering reference [22], thiazolidine (S)-2 (217 mg, 1.34 mmol) was dissolved in ethanol (10 mL) and heated to 78 • C under H 2 atmosphere. An excess of Raney Ni (approx.…”

Section: Attempt Bmentioning

confidence: 67%

Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines

et al. 2019

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A proof of concept for a novel approach towards enantiomerically highly enriched acyclic secondary amines and β-aminothiols as non-cyclic target molecules when starting from 3-thiazolines as heterocycles is presented. Starting from 2,2,4,5,5-pentamethyl-3-thiazoline, we demonstrated this chemoenzymatic pathway to both of these types of amine molecules, which were isolated as urea derivatives with a non-optimized yield of up to 20%. As a substrate, 2,2,4,5,5-pentamethyl-3-thiazolidine, which was obtained with an enantiomeric excess (ee) of 99% in a biotransformation from the corresponding 3-thiazoline according to a recently developed protocol, was used. For the reductive desulfurization of this substrate leading to a sulfur-free secondary amine, in situ formed Ni2B turned out to be a suitable reducing reagent. However, when using lithium aluminum hydride as a reducing agent, β-aminothiol was obtained.

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Section: Attempt Bmentioning

confidence: 67%

Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines

et al. 2019

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“…In yet another way to PhIP we envisioned the efficiently obtained 3 as a possible starting material. Indeed, reductive desulfurization of 3 by Raney nickel catalyst in refluxing ethanol-dioxane (1:1) or Raney nickel alloy (50:50 Al-Ni) [60] in refluxing dioxaneethanol-0.2 M NaOH (1:1:0.5) afforded PhIP in the modest yields of 25-35% (Scheme 6). Further, crucial for the reproducibility of this desulfurization to PhIP was the use of excess fresh Raney nickel.…”

Section: Björk and S Grivasmentioning

confidence: 99%

Synthesis of novel 2‐aminoimidazo[4,5‐b]pyridines, including the thieno analogue of the cooked‐food mutagen IFP

Björk¹,

Grivas²

2006

Journal of Heterocyclic Chem

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“…39 this procedure has its limitations since the hydrogenolysis reaction with RaNi is often incompatible with several functionalities, especially with sulphur containing structures [47]. Therefore we tried to replace this multi-step synthesis by a one-step arylation reaction starting from 3-amino-6chloropyridazine (1a).…”

Section: Mechanism Of the Suzuki Stille And Buchwald-hartwigmentioning

confidence: 99%