An efficient method for regioselective ring opening of epoxides by amines under microwave irradiation using Bi(NO3)3·5H2O as a catalyst

Bansal, Shobha; Kumar, Yogendra; Pippal, Parveen; Das, Dipak K.; Pramanik, Panchanan; Singh, Prabal Pratap

doi:10.1039/c6nj03701a

Cited by 11 publications

(5 citation statements)

References 33 publications

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“…2‐(Naphthalen‐1‐ylamino)‐2‐phenylethan‐1‐ol ( 4 g ) [30e] . Dark yellowish oil, yield: 257 mg (98 %).…”

Section: Methodsmentioning

confidence: 99%

Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis

Jain,

Satpute,

Jha

et al. 2023

Chemistry A European J

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A new series of unsymmetrical phenyl tellurides derived from 2‐N‐(quinolin‐8‐yl) benzamide ligand has been synthesized in a practical manner by the copper‐catalyzed method by using diaryl ditelluride and Mg as a reductant at room temperature. In order to augment the Lewis acidity of these newly formed unsymmetrical monotellurides, these have been transformed into corresponding unsymmetrical 2‐N‐(quinolin‐8‐yl)benzamide tellurium cations. Subsequently, these Lewis acidic tellurium cations were used as chalcogen bonding catalysts, enabling the synthesis of various substituted 1,2‐dihydroquinolines by activating ketones with anilines under mild conditions. Moreover, the synthesized 2‐N‐(quinolin‐8‐yl)benzamide phenyl tellurium cation has also catalyzed the formation of β‐amino alcohols in high regioselectivity by effectively activating epoxides at room temperature. Mechanistic insight by 1H and 19F NMR study, electrostatic surface potential (ESP map), control reaction in which tellurium cation reacted explosively with epoxide, suggested that the enhanced Lewis acidity of tellurium center seems responsible for efficient catalytic activities under mild conditions enabling β‐amino alcohols with excellent regioselectivity, trifluoromethyl, nitro‐substituted and bidentate monoanionic 1,2‐dihydroquinolines which were difficult to access.

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“…2‐(Naphthalen‐1‐ylamino)‐2‐phenylethan‐1‐ol ( 4 g ) [30e] . Dark yellowish oil, yield: 257 mg (98 %).…”

Section: Methodsmentioning

confidence: 99%

Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis

Jain,

Satpute,

Jha

et al. 2023

Chemistry A European J

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“…Later on, Bhanage [38] et al reported solvent free methodology for aminolysis of epoxides catalyzed by Y(NO 3 ) ⋅ 6H 2 O at room temperature (Figure 1), but these protocols suffered from some shortcomings for longer reaction time, tedious workup, costly and hazardous catalyst. In our earlier work [39] we reported regioselective and efficient protocol for the aminolysis of epoxides treated with low toxic, inexpensive and versatile nature of catalyst i. e. bismuth(III)nitrate pentahydrate, under solvent free microwave irradiation condition. Inspired by the results obtained, we intend to make an exhaustive study of other bismuth salts to add further meaningful insight in the catalytic behavior.…”

Section: Introductionmentioning

confidence: 99%

Environment Benign Bismuth Based Catalysts for the Expedite Regioselective Ring Opening of Epoxides Under Solvent Free Microwave Condition

Gupta,

Singh

2024

ChemistrySelect

Self Cite

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Bismuth‐based catalysts, namely Bi(PO4), (BiO)2CO3, BiF3, and Bi2(C2O4)3, are used as mild and efficient tools for the aminolysis of epoxides under solvent‐free conditions with microwave irradiation, which significantly reduced the reaction time. The catalysts employed are environment friendly, cost‐effective, and demonstrated high efficiency in terms of both high yields and regioselectivity.

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“…The asymmetric ring-opening (ARO) reaction of epoxides with amines is the most straightforward route to prepare β-amino alcohols. In recent years, several catalysts such as Lewis acids [11][12][13], metal-organic frameworks [14] and Bismuth (III) salts [15][16][17][18] have been reported for ring-opening reactions. However, these approaches usually require the use of costly reagents, high catalyst loadings, poor regioselectivity and also entail side effects, such as the rearrangement of epoxides to allyl alcohols under strong alkaline conditions or polymerization under strongly acidic conditions.…”

Section: Introductionmentioning

confidence: 99%

Ring-Opening of Epoxides with Amines for Synthesis of β-Amino Alcohols in a Continuous-Flow Biocatalysis System

Xue

Yang

et al. 2020

Catalysts

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An efficient method for the preparation of β-amino alcohols catalyzed by lipase TL IM from Thermomyces lanuginosus in a continuous-flow reactor was developed. The eco-friendly biocatalyst combined with continuous-flow reaction technology displayed high efficiency in the synthesis of β-amino alcohols. The benign reaction conditions (35 °C) and short residence time (20 min), together with the use of low cost and readily available starting materials, make this synthetic approach a promising alternative to current β-amino alcohol synthesis.

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An efficient method for regioselective ring opening of epoxides by amines under microwave irradiation using Bi(NO₃)₃·5H₂O as a catalyst

Cited by 11 publications

References 33 publications

Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis

Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis

Environment Benign Bismuth Based Catalysts for the Expedite Regioselective Ring Opening of Epoxides Under Solvent Free Microwave Condition

Ring-Opening of Epoxides with Amines for Synthesis of β-Amino Alcohols in a Continuous-Flow Biocatalysis System

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