Phosphomolybdic acid: a highly efficient solid acid catalyst for the synthesis of trans-4,5-disubstituted cyclopentenones

Reddy, B. V. Subba; Narasimhulu, G.; Lakshumma, P. Subba; Reddy, Y. V. R.; Yadav, J. S.

doi:10.1016/j.tetlet.2012.01.115

Cited by 40 publications

(12 citation statements)

References 39 publications

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“…19b Systematic mechanistic studies by the same group (2013 and 2015) 21,22 indicated that the reaction rate was controlled by a key off-cycle binding between aniline and catalyst. Since the seminal work, a range of catalytic systems, including those based on other Brønsted or Lewis acids, such as phosphomolybdic acid (Subba Reddy, 2012), 23 BF 3 •Et 2 O (Afonso and Caddick, 2013), 24 Ca(NTf 2 ) 2 (Schulz and Gandon, 2014; Leboeuf and Gandon, 2016), 25 and aryl boronic acid (Zheng, 2017), 26 have also been developed for triggering aza-Piancatelli reactions.…”

Section: Diastereoselective Oxa-/aza-piancatelli Reactionsmentioning

confidence: 99%

Recent Advances on Piancatelli Reactions and Related Cascade Processes

Zhong¹,

Xu²,

Cai³

2021

Synthesis

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The Piancatelli reaction, which is the rearrangement of 2-furylcarbinol to cyclopentenone, involves a key furanoxonium ion intermediate and a furan ring opening-4π electrocyclization process. In recent years, the original oxa-Piancatelli reaction has been extended to a large family of aza- and carbo-Piancatelli reactions and related cascade processes, providing a powerful platform for the construction of diverse functionalized cyclopentenones and polycyclic cyclopentanones. Meanwhile, chiral Brønsted/Lewis acid based catalytic asymmetric approaches to Piancatelli reactions have also been achieved for the assembly of highly valued chiral cyclopentenone scaffolds. In this short review, we present an overview of the recent developments in these areas and focus primarily on reports published in the last five years.1 Introduction2 Diastereoselective Oxa-, Aza- and Carbo-Piancatelli Reactions3 Diastereoselective Cascade Piancatelli Reactions4 Asymmetric Piancatelli Reactions and Related Cascade Processes5 Miscellaneous Furanoxonium Ion-Based Rearrangements6 Conclusion

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Section: Diastereoselective Oxa-/aza-piancatelli Reactionsmentioning

confidence: 99%

Recent Advances on Piancatelli Reactions and Related Cascade Processes

Zhong¹,

Xu²,

Cai³

2021

Synthesis

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“…The reaction was successful with sterically hindered 2,4,6-trimethylaniline (35e, 35g, 35i, 35k), while a competitive Friedel-Craft alkylation occurred when 2,6-dimethylaniline was employed delivering 36 and 37 (Scheme 16). Subba Reddy et al [49] performed the aza-Piancatelli rearrangement using phosphomolybdic acid (PMA) as the catalyst (0.03 mol %) in acetonitrile at reflux, isolating trans-4-amino-5-substituted cyclopent-2-enones in greater than 80% yield, in about 1 h.…”

Section: Intermolecular Aza-piancatelli Rearrangementmentioning

confidence: 99%

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

2013

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Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter-and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.

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“…Several excellent review literature on the conversion of cellulose have been reported, with focus on the discussion of different solid acid catalysts (e.g., Kobayashi et al, 2010;Pang et al, 2010;Rinaldi et al, 2010;Tian et al, 2010Tian et al, , 2011Wu et al, 2010;Akiyama et al, 2011;Komanoya et al, 2011;Lai et al, 2011;Ogasawara et al, 2011;Zhang et al, 2011). Compared with other solid acids, HPA catalysts are more favorable for hydrolysis of cellulose, considering that they have some unique properties such as stronger acidity compared to other mineral acids (e.g., H 2 SO 4 , HCl), high redox properties, good thermal stability, easy separation, good reusability, fewer side products, less waste generation, non-toxicity, and easy handling, as illustrated in Figure 1 (Kozhevnikov, 1987(Kozhevnikov, , 1998Mizuno and Misono, 1994;Kaur and Kozhevnikov, 2002; et al., 2009a;Yang et al, 2011;Deng et al, 2012;Reddy et al, 2012;de Op Beeck et al, 2013). Furthermore, HPA catalysts can be used in both homogeneous and heterogeneous systems.…”

Section: Introductionmentioning

confidence: 99%

Heteropoly Acid-Based Catalysts for Hydrolytic Depolymerization of Cellulosic Biomass

Luo

et al. 2020

Front. Chem.

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Cellulose is the most abundant source of biomass, which can be converted into monosaccharide or other chemical platform molecules for the sustainable production of chemicals and fuels. Acid catalysts can promote hydrolytic degradation of cellulose into valuable platform molecules, which is of great significance in the development of chemicals and biofuels. However, there are still some shortcomings and limitations of the catalysts for the hydrolytic degradation of cellulosic biomass. Heteropoly acid (HPA), as a green catalyst, seems to be more conducive to the degradation of cellulosic biomass due to its extreme acidity. HPAs can be designed in homogeneous and heterogeneous systems. Moreover, they can be easily separated from the products in both systems by a simple extraction process. According to the unique properties of HPAs (e.g., good solubility, high thermal stability, and strong acidity), using heteropoly acid-based catalysts to depolymerize and convert cellulose into value-added chemicals and biofuels has become one of the most remarkable processes in chemistry for sustainability. In this review, the characteristics, advantages, and applications of HPAs in different categories for cellulose degradation, especially hydrolysis hydrolytic degradation, are summarized. Moreover, the mechanisms of HPAs catalysts in the effective degradation of cellulosic biomass are discussed. This review provides more avenues for the development of renewed and robust HPAs for cellulose degradation in the future.

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Phosphomolybdic acid: a highly efficient solid acid catalyst for the synthesis of trans-4,5-disubstituted cyclopentenones

Cited by 40 publications

References 39 publications

Recent Advances on Piancatelli Reactions and Related Cascade Processes

Recent Advances on Piancatelli Reactions and Related Cascade Processes

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

Heteropoly Acid-Based Catalysts for Hydrolytic Depolymerization of Cellulosic Biomass

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