New Methods for the Preparation of Aromatic Aldehydes

Kantlehner, Willi

doi:10.1002/ejoc.200200653

Cited by 57 publications

(35 citation statements)

References 40 publications

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“…Among other synthetic methods, they can be obtained from the corresponding primary aromatic amines, which are readily available substrates. Methods for the oxidation of amines to carbonyl compounds have received significant attention, but these approaches are frequently poorly sustainable, because they produce waste and by‐products that are difficult to recycle, require drastic reaction conditions, and often proceed with poor selectivity …”

Section: Introductionmentioning

confidence: 98%

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

et al. 2017

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A new mild and efficient process for the aqueous preparation of aldehydes, which are employed as flavour and fragrance components in food, beverage, cosmetics, as well as in pharmaceuticals, was developed using a continuous‐flow approach based on an immobilised pure transaminase‐packed bed reactor. HEWT, an ω‐transaminase from the haloadapted bacterium Halomonas elongata, has been selected for its excellent stability and substrate scope. Sixteen different amines were rapidly (3–15 min) oxidised to the corresponding aldehydes (90 to 99 %) with only 1 to 5 equivalents of sodium pyruvate. The process was fully automated, allowing for the in‐line recovery of the pure aldehydes (chemical purity >99 % and isolated yields above 80 %), without any further work‐up procedure.

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Section: Introductionmentioning

confidence: 98%

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

et al. 2017

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“…In particular, we envisaged that by exploiting the conversion of the nitro to carbonyl group, the Nef reaction, this method would represent a novel, mild formylation orthogonal to Friedel Crafts and lithiation/formylation transforms. 5 Furthermore, nitromethane is more easily deployed as a formyl equivalent on a small scale compared to carbon monoxide, a toxic gas that requires tanks and often high temperatures and pressures. 6 Herein, we describe the Pd-catalyzed coupling of aryl halides with nitromethane to afford arylnitromethanes and subsequent Sn(II)-mediated Nef reaction to provide aryl oximes or aryl aldehydes.…”

mentioning

confidence: 99%

Palladium-Catalyzed Nitromethylation of Aryl Halides: An Orthogonal Formylation Equivalent

2012

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An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups.

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“…Additionally, aromatic aldehydes are also potent intermediates in fine chemicals synthesis . Hence, their preparations have been the core interest of synthetic chemists for a long time . Traditional synthetic methods are mainly based on acylation of aromatic compounds with two types of strategies.…”

Section: Methodsmentioning

confidence: 99%

A Convenient Palladium‐Catalyzed Reductive Carbonylation of Aryl Iodides with Dual Role of Formic Acid

2016

Chemistry A European J

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Palladium-catalyzed reductive carbonylation of aryl halides represents a straightforward pathway for the synthesis of aromatic aldehydes. The known reductive carbonylation procedures either require CO gas or complexed compounds as CO sources. In this communication, we developed a palladium-catalyzed reductive carbonylation of aryl iodides with formic acid as the formyl source. As a convenient, practical, and environmental friendly methodology, no additional silane or H2 was required. A variety of aromatic aldehydes were isolated in moderate to excellent yields under mild reaction conditions. Notably, this is the first procedure on using formic acid as the formyl source.

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New Methods for the Preparation of Aromatic Aldehydes

Abstract: This review aims to provide an overview of the use of oligoformylamine derivatives and related compounds as formylating reagents for aromatic compounds. The synthesis of aromatic aldehydes by means of Fries rearrangement of aryl formates is also reported on.

Cited by 57 publications

References 40 publications

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

Palladium-Catalyzed Nitromethylation of Aryl Halides: An Orthogonal Formylation Equivalent

A Convenient Palladium‐Catalyzed Reductive Carbonylation of Aryl Iodides with Dual Role of Formic Acid

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