Bulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O2 to Give Enamines

Zhou, Yibo; Angelici, Robert J.; Woo, L. Keith

doi:10.1007/s10562-010-0339-7

Cited by 19 publications

(20 citation statements)

References 68 publications

(113 reference statements)

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“…155 This reaction, which occurs in high yields (58-94%), is interesting because no report of other catalytic system is known and the process is quite simple to apply.…”

Section: Oxidation Of Aminesmentioning

confidence: 99%

Update on selective oxidation using gold

2012

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This critical review aims to update the recent development in the selective oxidation of organic compounds by gold catalysis, highlighting the progress in the last three years. Following the impressive developments in the last decades, several protocols for catalytic oxidation are today available, which are based on the extraordinary properties of gold in terms of catalytic activity, selectivity, reusability and resistance to poisons. Beside many other applications, gold can be recommended for green processes dedicated to fine chemicals, pharmaceuticals and the food industry owing to its recognized bio-compatibility. The collected literature is focused on experiments concerning the oxidation of different chemical groups and could be of interest, in the wide area of organic chemistry, for improving previous processes or for exploring new catalytic pathways (174 references).

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“…155 This reaction, which occurs in high yields (58-94%), is interesting because no report of other catalytic system is known and the process is quite simple to apply.…”

Section: Oxidation Of Aminesmentioning

confidence: 99%

Update on selective oxidation using gold

2012

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“…However, our group has recently found that bulk gold also catalyzes several oxidations in which O 2 is the oxidant. These include the reaction of isocyanides with amines to produce carbodiimides [8] or ureas [9], reactions of carbon monoxide with primary amines to afford ureas [10], and reactions of diazoalkanes with amines to give enamines [11]. In addition, bulk gold catalyzes the oxidative dehydrogenation of amines to imines using O 2 as the oxidant (Eqs.1-3) [12,13].…”

Section: Introductionmentioning

confidence: 99%

Bulk Gold-Catalyzed Oxidations of Amines and Benzyl Alcohol Using Amine N-Oxides as Oxidants

2012

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Bulk gold powder (*50 lm) catalyzes the oxidative dehydrogenation of amines to give imines using amine N-oxides (R 3 N-O) as the oxidant. The reaction of dibenzylamine (PhCH 2 -NH-CH 2 Ph) with N-methylmorpholine N-oxide (NMMO) in the presence of gold powder at 60°C produced N-benzylidenebenzylamine (PhCH=N-CH 2 Ph) in 96% yield within 24 h. Benzyl alcohol was oxidized by NMMO to benzaldehyde in[60% yield in the presence of gold powder. Although O 2 was previously shown to oxidize amines in the presence of bulk gold, it is surprising that gold is also capable of catalyzing the oxidation of amines using amine oxides, which are chemically so different from O 2 .

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“…The engineering of designer surfaces functionalized with carbenes [50,51,[216][217][218], and the redox properties and intervalence charge transfer of such organometallic systems on electrode surfaces [219] are other rapidly expanding focus areas. A class of multimetal multicarbene complexes with great potential includes those with a large number of carbene ligands found in close proximity to each other in macromolecular assemblies or surfaces.…”

Section: Discussionmentioning

confidence: 99%