Boric Acid: A Versatile Catalyst in Organic Synthesis

Pathan, Shahebaaz K.; Mahaparale, Paresh; Deshmukh, Satish U.; Une, Hemant D.; Sangshetti, Jaiprakash N.

doi:10.1007/978-3-030-44176-0_17

Cited by 4 publications

(5 citation statements)

References 57 publications

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“…For the synthesis of various heterocyclic compounds from active methylene compounds, the Knoevenagel condensation product was obtained as an intermediate or it was deemed one of the major impurities formed during the reaction due to a slight excess of reagents [4][5][6][7][8][9][10]. Therefore, synthesizing such an intermediate is crucial.…”

Section: Resultsmentioning

confidence: 99%

“…It serves as a fundamental method for creating carboncarbon bonds, playing a crucial role in the production of pharmaceutically and biologically active compounds [2,3]. In various organic transformations, boric acid has proven to be an effective catalyst (Figure 1) [4][5][6][7][8][9][10]. Its catalytic properties have been exploited in numerous reactions, including decarboxylation, bromination, amidation, esterification, trans-esterification, β-acetamido ketone synthesis, condensation reactions, ipso-hydroxylation, Mannich reactions, aza-Michael addition, and Biginelli reactions, among others.…”

Section: Introductionmentioning

confidence: 99%

“…Its catalytic properties have been exploited in numerous reactions, including decarboxylation, bromination, amidation, esterification, trans-esterification, β-acetamido ketone synthesis, condensation reactions, ipso-hydroxylation, Mannich reactions, aza-Michael addition, and Biginelli reactions, among others. The versatility of boric acid as a catalyst underscores its importance in facilitating diverse synthetic processes [4][5][6][7][8][9][10]. Multiple mechanisms involving Bronsted acid catalysis have been proposed for the Knoevenagel condensation process (Figure 2) [4].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

One-Pot Synthesis of Knoevenagel Condensation Products Using Boric Acid as a Catalyst

Thorat,

Thakare,

Mhaske

et al. 2023

The 4th International Electronic Conference on Applied Sciences

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

One-Pot Synthesis of Knoevenagel Condensation Products Using Boric Acid as a Catalyst

Thorat,

Thakare,

Mhaske

et al. 2023

The 4th International Electronic Conference on Applied Sciences

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“…Our initial investigations began from promising results obtained in a planetary ball mill. For our first trials, boric acid was selected as a moderate-strength, known effective carbonyl and imine activator, and eco-friendly solid replacement for the liquid acid (TFA) used in the solution-based methodology . The usage of readily available Schwartz’s reagent directly delivered unpromising results, so the strategy turned to the in situ generation of the zirconium-based reductant from inexpensive zirconocene dichloride and lithium tri- tert -butoxyaluminum hydride (LTBA), previously reported in solution by Snieckus .…”

Section: Resultsmentioning

confidence: 99%

From Flask to Mill: Reductive Functionalization of Fluoroacetamides as a Case Study for Transferring Solvent-Based Reactions to the Solid State

Czerwiński

Najczuk

Furman

2022

ACS Sustainable Chem. Eng.

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The development of sustainable methods is a central focus of modern organic synthesis and has applications in various areas of the chemical industry. Mechanochemistry is a highly desirable green synthetic method as it departs from traditional solution-based reactions and their concurrent generation of waste solvent. Here, we report results of the adaptation of a solutionbased method for the reductive functionalization of fluoroacetamides to a mechanochemical protocol as a case study. This greener solid-state, one-pot strategy is based on the partial reduction of amides by an in situ mechanochemically generated zirconocene chloride hydride (Schwartz's reagent) and tandem nucleophilic addition of indole to afford high-value functionalized fluorinated amines in moderate to good yields. In addition to it being the first time this reductant has been mechanochemically generated, the sustainable approach was complemented by operationally simple purification by an acidic resin. Significant improvements in green metrics (E factor and EcoScale) were observed by this adaptation of the methodology.

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“…Boric acid, due to its environmentally benign physicochemical properties combined with its easy commercial availability, has recently gained exceptional interest in organic synthesis as a substitute for conventional acid catalytic materials. In this context, boric acid has proved to be particularly versatile, having been shown to catalyze an extensive array of organic transformations, such as halogenation reaction, amidation, esterification, the metal-organic framework, Aza-Michael addition, bromination of a variety of organic substrates, ipso-hydroxylation, and transesterification [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Towards Advances in Molecular Understanding of Boric Acid Biocatalyzed Ring-Opening (Co)Polymerization of δ-Valerolactone in the Presence of Ethylene Glycol as an Initiator

et al. 2021

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Following our previous studies on the molecular level structure of (co)oligoesters obtained via anionic homo- and co-polymerization of novel β-substituted β-lactones, prepared by the atmospheric pressure carbonylation reaction of respective epoxides, the boric acid biocatalyzed ring-opening (co)polymerization of δ-valerolactone has been studied. As a co-monomer the 6-methy-ε-caprolactone, prepared by the one-pot oxidation of respective alcohol, and ethylene glycol as polymerization initiator were used. The obtained copolymers were characterized by 1H-NMR, GPC and ESI-MS, respectively in order to confirm their chemical structures and identity. Subsequently, tandem mass spectrometry (MS-MS studies) via collision-induced dissociation were utilized to characterize the fragmentation pattern. ESI-MS and NMR analyses confirmed the formation of random linear copolymer chains composed of different polyester repeat units. MS-MS experiments showed that fragmentation proceeds via ester bound cleavage along the (co)polyester chains. The innovative aspect of this contribution is related to the elaboration of the telechelic (co)polymers end-capped with hydroxyl end groups and well-defined molecular architectures, which could facilitate the development of new flexible macromolecular systems for potential biomedical applications.

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Boric Acid: A Versatile Catalyst in Organic Synthesis

Cited by 4 publications

References 57 publications

One-Pot Synthesis of Knoevenagel Condensation Products Using Boric Acid as a Catalyst

One-Pot Synthesis of Knoevenagel Condensation Products Using Boric Acid as a Catalyst

From Flask to Mill: Reductive Functionalization of Fluoroacetamides as a Case Study for Transferring Solvent-Based Reactions to the Solid State

Towards Advances in Molecular Understanding of Boric Acid Biocatalyzed Ring-Opening (Co)Polymerization of δ-Valerolactone in the Presence of Ethylene Glycol as an Initiator

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