Lemon Juice: A Versatile Biocatalyst and Green Solvent in Organic Transformations DOI
Baji Baba Shaik, Pule Seboletswe, Sachin Balaso Mohite

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(5)

Published: Feb. 1, 2022

Abstract Green chemistry is the basis for fast‐growing, eco‐friendly, alternative sustainable technologies development of chemical products without use or generation hazardous catalysts. The role naturally occurring fruit juice as a catalyst solvent in organic synthesis has gained focused interest across globe. Lemon juice‐mediated been widely explored recently highly significant, selective and biocatalyst synthesis. This review presents recent developments on lemon‐juice mediated transformations their application to synthesize molecules building blocks pharmaceutical interest. We believe this article will be researchers both academic industrial settings developing novel pharmacophores from green principles perspective.

Language: Английский

Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State‐of‐The‐Art Survey DOI
Ming Xiang, Dana E. Pfaffinger, Michael J. Krische

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(52), P. 13107 - 13116

Published: June 29, 2021

Abstract The use of allenes and 1,3‐dienes as chiral allylmetal pronucleophiles in intermolecular catalytic enantioselective reductive additions to aldehydes, ketones, imines, carbon dioxide other C=X electrophiles is exhaustively catalogued together with redox‐neutral hydrogen auto‐transfer processes. Coverage limited processes that result both C−H C−C bond formation. alkynes latent multicomponent allylations involving dienes not covered. As illustrated this review, the ability serve tractable non‐metallic has evoked many useful transformations have no counterpart traditional chemistry.

Language: Английский

Citations

67

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol DOI
Colton R. Davis,

Irungu K. Luvaga,

Joseph M. Ready

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(13), P. 4921 - 4927

Published: March 23, 2021

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C–C bond and sets 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension trisubstituted olefins three contiguous stereocenters.

Language: Английский

Citations

63

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis DOI Creative Commons
Brenno A. D. Neto,

Rafael O. Rocha,

Marcelo O. Rodrigues

et al.

Molecules, Journal Year: 2021, Volume and Issue: 27(1), P. 132 - 132

Published: Dec. 27, 2021

In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields shortening reaction times, is vital achieving greener protocols furthering MCR field research. Considering that MCRs typically have two or more possible pathways explain transformation, essential for selecting a route avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts reagent quantities, were analyzed. Solvent effects, which are likely most neglected topic in MCRs, well their catalysis, critically discussed. Stereocontrolled rarely observed without presence catalytic system, also presented discussed review. Perspectives on use systems improved finally presented.

Language: Английский

Citations

59

Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions DOI Creative Commons
Shanglin Chen, Yanan Wang,

Jinhui Xie

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: June 28, 2024

1,2-Difunctionalization of alkynes offers a straightforward approach to access polysubstituted alkenes. However, simultaneous multi-component cascade transformations including difunctionalization two with both syn- and anti-selectivity in one catalyst system is undeveloped proves be significant challenge. Herein, we report Nickel-catalyzed four-component reaction 1,3-dienes using terminal alkynes, aryl boroxines, perfluoroalkyl iodides, wherein the forms three new C-C bonds single vessel serve as modular strategy excellent chemoselectivity, good regioselectivity exclusive stereoselectivity. Control experiments reveal plausible mechanism DFT calculations explain cause for formation this unusual reaction. Furthermore, successfully incorporate biologically active units into 1,2,3,4-tetrasubstituted 1,3-dienes, which greatly increases diversity molecular scaffolds brings more potential values medicinal chemistry, synthetic utility our protocol further demonstrated by late-stage transformations.

Language: Английский

Citations

9

Copper- and Palladium-Cocatalyzed Chemo-, Regio-, Stereo-, and Atroposelective Arylboration of 1,3-Enynes DOI
Wangyang Li, Haohua Chen,

Yanping Zheng

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11318 - 11331

Published: July 15, 2024

Catalytic enantioselective borylation reactions of unsaturated bonds as powerful tools for the synthesis diverse chiral organoboron compounds have gained much attention and wide applications in various fields. However, atroposelective arylboration reaction with carbon–carbon triple 1,3-enynes to obtain axially 1,3-dienylboronates remains an elusive significant challenge. Hence, we develop a cooperative copper- palladium-catalyzed assemble plentiful function enriched single step from easily available 1,3-enynes, B2pin2, aryl bromides high levels chemo-, regio-, stereo-, atroposelectivity. The mild conditions lead good functional group tolerance, which is proven by broad substrate scope late-stage functionalizations bioactive or drug molecules. Moreover, can be scaled up, series further transformations achieved. It worth emphasizing that several olefin catalysts ligands axial chirality also synthesized through corresponding elaborations such products, explains transformative ability application potential 1,3-dienylboronates. mechanism experiment density theory (DFT) calculations revealed process copper palladium catalysis, indicating chemoselectivity regioselectivity boration are determined enyne insertion on copper, atroposelectivity controlled reductive elimination center. Meanwhile, calculation demonstrated distinct interactions between P═O C═O groups Pd Bpin center key transition state formation products varying configurations while employing identical configuration ligands.

Language: Английский

Citations

8

Recent developments in the asymmetric synthesis and functionalization of symmetrical and unsymmetricalgem-diborylalkanes DOI

Swagata Paul,

Kanak Kanti Das,

Debasis Aich

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(3), P. 838 - 852

Published: Nov. 16, 2021

gem -Diborylalkanes are an important class of organoboron compounds as they function a key building block in organic synthesis. This review summarizes recent developments the enantioselective synthesis -diborylalkanes and application asymmetric

Language: Английский

Citations

43

Fe3O4@SiO2-PMA-Cu magnetic nanoparticles as a novel catalyst for green synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles DOI Creative Commons
Ronak Eisavi, Fereshteh Ahmadi

Scientific Reports, Journal Year: 2022, Volume and Issue: 12(1)

Published: July 13, 2022

The magnetic nanoparticles of Fe3O4 were synthesized through a solid-state reaction hydrated iron (III) chloride, (II) chloride and NaOH, then purified by calcination at high temperature. In order to protect ferrite from oxidation agglomeration, manufacture novel catalytic system anchored copper on the substrate, was core-shelled adding tetraethyl orthosilicate. Next, prepared Fe3O4@SiO2 supported phosphomolybdic acid (PMA) as second layer nanocomposite 80 °C in 30 h. Eventually, new Fe3O4@SiO2-PMA-Cu successfully solution solid potassium borohydride. structure nanocatalyst acknowledged different techniques such EDS, VSM, XRD, TEM, FT-IR, XPS, TGA, BET FESEM. synthesis β-thiolo/benzyl-1,2,3-triazoles various thiiranes, terminal alkynes sodium azide catalyzed aqueous medium. obtain optimum condition, effects time, temperature, catalyst amount solvent gauged. recycled used for several consecutive runs without any loss activity.

Language: Английский

Citations

37

Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes DOI Creative Commons
Shengnan Jin, Jinxia Li, Kang Liu

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: June 20, 2022

Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack direct synthetic protocols. Therefore, it is very challenging to develop a simple effective strategy obtain 1,1-diborylalkanes. Herein, we an enantioselective copper-catalyzed cascade double hydroboration terminal alkynes highly enantioenriched gem-diborylalkanes were readily obtained. Our uses two different boranes construct valuable gem-bis(boryl) alkanes with one catalytic ligand pattern, which represents simplest most straightforward for constructing such gem-diborons.

Language: Английский

Citations

36

A new avenue for the preparation of organoboron compounds via nickel catalysis DOI
Samir Manna, Kanak Kanti Das,

S. K. NANDY

et al.

Coordination Chemistry Reviews, Journal Year: 2021, Volume and Issue: 448, P. 214165 - 214165

Published: Aug. 29, 2021

Language: Английский

Citations

36

Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence DOI Creative Commons
Yuanqi Wu,

Lizuo Wu,

Zhan‐Ming Zhang

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(7), P. 2021 - 2025

Published: Jan. 1, 2022

A palladium catalyzed enantioselective Heck/borylation reaction of alkene-tethered aryl iodides was realized, delivering a variety 2,3-dihydrobenzofuranyl boronic esters in high yield with excellent enantioselectivity.

Language: Английский

Citations

27