Highly efficient synthesis of primary amides <i>via</i> aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex

Yang, Fa‐Liu; Zhu, Xinju; Rao, Dun‐Kang; Cao, Xiao-Niu; Li, Ke; Xu, Yan; Hao, Xin‐Qi; Song, Mao‐Ping

doi:10.1039/c6ra07515k

Cited by 32 publications

(12 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In this line, Hao and Song describe a protocol to obtain primary amides under mild conditions . This strategy consists in the rearrangement of aldoximes promoted by NNN–Ru pincer complex 101 (Scheme ).…”

Section: Cross‐coupling Reactionsmentioning

confidence: 99%

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

et al. 2018

View full text Add to dashboard Cite

Pincer complexes are useful tools for organic synthesis. Their high stability and easy functionalization have allowed the development of novel catalytic systems that have had a tremendous impact in different areas of chemistry. Thus, catalytic reactions are nowadays a fundamental part of several synthetic routes, as they allow “greener” procedures with high atom efficiency. In this context, pincer complexes have contributed to the establishment of novel and efficient catalytic reactions. Thus, herein we summarize the most recent relevant advances involving pincer complexes as catalysts.

show abstract

Section: Cross‐coupling Reactionsmentioning

confidence: 99%

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Arene–ruthenium(II) complexes were also proved to be appropriate catalysts for the rearrangement of aldoximes generated in situ from the corresponding aldehydes. Recently, Song and co‐workers described a complexed ionic ruthenium pincer catalyst was applicable for the synthesis of amides from aldoximes . Nevertheless, compared with the rapid development of ruthenium catalyst, there existed few reports on the rearrangement of aldoximes utilizing rhodium catalysts.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Protocol for the Synthesis of Primary Amides via Rh‐Catalyzed Rearrangement of Aldoximes

Song

et al. 2018

ChemistrySelect

View full text Add to dashboard Cite

A system consisting of catalytic amounts of [Rh(CH 2 = CH 2 )Cl] 2 / PPh 2 Cy, and PhCl as the solvent efficiently catalyzes selective rearrangement of aldoximes to furnish various primary amides in moderate to good yields. Replacing the [Rh(CH 2 = CH 2 )Cl] 2 with Rh(NBD) 2 OTf enables the superior transformation to afford the amides with up to 99% yields. Attractive synthetic features associated with this methodology include absence of cocatalysts, broad functional group tolerance, good to excellent yields, low metal loadings, and operational convenience.[a] Dr.

show abstract

“…developed a series of ionic ruthenium complexes and found that tridentate complex 65 showed high catalytic activity for the rearrangement of aldoximes into primary amides under mild conditions (Scheme a). This reaction proceeded in water at 110 °C for 12 h . A range of aromatic, heteroaromatic, and conjugated aldoximes were found to be suitable substrates for this transformation, thereby giving the desired amides in good‐to‐high yields with excellent functional‐group compatibility.…”

Section: Synthesis Of Amides From Oximesmentioning

confidence: 99%

Carbonyl Compounds′ Journey to Amide Bond Formation

Reddy

Beatriz

Lima

2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

The formation of amide bonds is one of the most stimulating emerging areas in organic and medicinal chemistry.A mides are recognized as central building blocks in a plethora of interesting pharmaceuticals, proteins, peptides, polymers, naturalp roducts, functional materials, andb iologically relevant carbocyclic or heterocyclic molecules, and they are also found in av ariety of industrial fields. Therefore, a review of recent developments and challenges in the formation of amide bonds from carbonyl compounds is particular-ly important. Herein, we have scrutinized ar ange of metalcatalyzed andm etal-free approaches for the synthesis of amides from aldehydes, ketones, and oximes. In addition, this Minireview highlightsr elevant mechanistic studies, as well as the potential applications of these methods in the synthesis of candidate drug molecules. We hope that the data compiled herein will encourage further progress in this notable area of chemistry research.

show abstract

Highly efficient synthesis of primary amides via aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex

Abstract: An ionic Ru pincer complex was demonstrated to be highly efficient catalyst for conversion of aldoximes and aldehydes into corresponding primary amides with environmental benignity, operational convenience and catalytic loading as low as 0.5 mol%.

Cited by 32 publications

References 49 publications

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

An Efficient Protocol for the Synthesis of Primary Amides via Rh‐Catalyzed Rearrangement of Aldoximes

Carbonyl Compounds′ Journey to Amide Bond Formation

Contact Info

Product

Resources

About