Rapid aminations of functionalized aryl fluorosulfates in water DOI
Karthik S. Iyer,

Kylee B. Dismuke Rodriguez,

R.M. Lammert

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(43)

Published: July 22, 2024

Abstract Aryl fluorosulfates of varying complexities have been used in amination reactions water using a new Pd oxidative addition complex ( OAC‐1 ) developed specifically to match the needs fine chemicals industry, not only terms functional group tolerance, but also reflecting time considerations associated with these important C−N couplings. Also especially noteworthy is that they replace both PFAS‐related triflates and nonaflates, which are today out favor due recent government regulations. The based on BippyPhos ligand at low loadings under aqueous micellar conditions. Moreover, it easily prepared stable long term storage. DFT calculations OAC precatalyst compare well X‐ray structure crystals π‐complexation aromatic system confirm NMR data showing mixture conformers solution differ from rotation phenyl t ‐butyl substituents. An extensive variety coupling partners, including pharmaceutically relevant APIs, readily participate mild environmentally responsible reaction

Language: Английский

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives DOI Creative Commons
Andrew Jordan, Callum G. J. Hall,

Lee R. Thorp

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(6), P. 6749 - 6794

Published: Feb. 24, 2022

Dipolar aprotic and ethereal solvents comprise just over 40% of all organic utilized in synthetic organic, medicinal, process chemistry. Unfortunately, many the common "go-to" are considered to be "less-preferable" for a number environmental, health, safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or practical handling flammability volatility. Recent legislative changes have initiated implementation restrictions on use commonly employed dipolar dimethylformamide (DMF) N-methyl-2-pyrrolidinone (NMP), ethers 1,4-dioxane. Thus, with growing legislative, EHS, societal pressures, need identify implement alternative that greener, safer, more sustainable has never been greater. Within this review, ubiquitous nature is discussed respect physicochemical properties made them so appealing chemists. An overview current being imposed discussed. A variety alternative, garnered attention past decade then examined, case studies examples where less-preferable successfully replaced safer highlighted. Finally, general guidance solvent selection replacement included Supporting Information review.

Language: Английский

Citations

116
Aqueous Micelles as Solvent, Ligand, and Reaction Promoter in Catalysis DOI Creative Commons

Jagdeep K. Virdi,

Ashish Dusunge,

Sachin Handa

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(2), P. 301 - 317

Published: Jan. 16, 2024

Water is considered to be the most sustainable and safest solvent. Micellar catalysis a significant contributor chemistry in water. It promotes pathways involving water-sensitive intermediates transient catalytic species under micelles' shielding effect while also replacing costly ligands dipolar-aprotic solvents. However, there lack of critical information about micellar catalysis. This includes why it works better than traditional organic solvents, specific rules differ from those conventional catalysis, how limitations can addressed future. Perspective aims highlight current gaps our understanding provide an analysis designer surfactants' origin essential components. will fundamental including aqueous micelles simultaneously perform multiple functions such as solvent, ligand, reaction promoter.

Language: Английский

Citations

29
Towards a sustainable tomorrow: advancing green practices in organic chemistry DOI
Sudripet Sharma, Fabrice Gallou, Sachin Handa

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6289 - 6317

Published: Jan. 1, 2024

Chemistry in water, leveraging its solvent properties, provides a safer and more sustainable alternative to traditional organic methods.

Language: Английский

Citations

23
Selectivity in micellar catalysed reactions: The role of interfacial dipole, compartmentalisation, and specific interactions with the surfactants DOI Creative Commons
Sara Mattiello, Erika Ghiglietti, Anita Zucchi

et al.

Current Opinion in Colloid & Interface Science, Journal Year: 2023, Volume and Issue: 64, P. 101681 - 101681

Published: Feb. 13, 2023

Micellar catalysis is playing a major role in green chemistry with ever increasing applications the efficient and sustainable preparation of natural compounds, drugs, more recently organic semiconductors for printed electronics.Most contributions field focus on developments surfactants suitable formulative conditions capable reproducingand often improvingthe yield reactions commonly performed solvents.The real ambition micellar approach goes beyond improvement sustainability existing methods aims at mimicking not only efficiency but also selectivity enzymatic catalysis.This review summarizes relevant examples enabled, efficient, selective transformations, discusses different kind processes impacting product distribution depending details state achieved.

Language: Английский

Citations

20
Implementation of micelle-enabled C(sp2)–C(sp3) cross-electrophile coupling in pharmaceutical synthesis DOI
Bin Wu, Ning Ye, Kangming Zhao

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(17), P. 2349 - 2352

Published: Jan. 1, 2024

A sustainable C(sp 2 )–C(sp 3 ) cross-electrophile coupling was developed between readily available 5-bromophthalide and 1-benzyl-4-iodopiperidine under micellar conditions, leading to a key intermediate of one our development compounds.

Language: Английский

Citations

8
Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us DOI
Pascal Hauk, Joanna Wencel‐Delord, Lutz Ackermann

et al.

Current Opinion in Colloid & Interface Science, Journal Year: 2021, Volume and Issue: 56, P. 101506 - 101506

Published: Sept. 21, 2021

Language: Английский

Citations

41
Simplified Preparation of ppm Pd-Containing Nanoparticles as Catalysts for Chemistry in Water DOI Creative Commons
Yuting Hu, Xiaohan Li, Gongzhen Jin

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(5), P. 3179 - 3186

Published: Feb. 17, 2023

A protocol has been developed that not only simplifies the preparation of nanoparticles (NPs) containing ppm levels ligated palladium affect heterogeneous catalysis but also ensures they afford products cross-couplings reproducibly due to freshly prepared nature each reagent. Four different types couplings are studied: Suzuki-Miyaura, Sonogashira, Mizoroki-Heck, and Negishi reactions, all performed under mild aqueous micellar conditions. The simplified process relies on initial formation stable, storable Pd- ligand-free NPs, which is then added appropriate amount Pd(OAc)2 ligand-matched desired type coupling, in water.

Language: Английский

Citations

16
Photoredox-catalyzed coupling of acyl oxime acetates with thiophenols to give arylthioesters in water at room temperature DOI

Yuanyuan Fu,

Shengzhen Zhu, Xueyan Zhao

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(18), P. 6849 - 6853

Published: Jan. 1, 2022

A convenient synthesis of valuable arylthioesters via visible-light-induced radical coupling acyl oxime acetates with thiophenols in water was developed.

Language: Английский

Citations

15
Micelles Enabled Nickel-Catalyzed P-Arylation of Aromatic Phosphine Oxide in Water Under Mild Conditions DOI

Pritesh Keshari,

Rajan Yadav,

Priya Mata

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(31), P. 11473 - 11479

Published: July 15, 2024

A nonionic surfactant has been developed from agricultural waste and its potential application for the Ni-catalyzed C–P cross-coupling reaction in water. The was fully characterized by various spectroscopic imaging techniques. size of micelles morphological changes presence catalysts/substrates were established using transmission electron microscopy (TEM), dynamic light scattering (DLS), confocal microscopy. Controlled 31P NMR, 19F mass spectrometry, X-ray photoelectron spectroscopy (XPS) analysis revealed possible reactive intermediates mechanisms. synthesis shown 20 g 1 scale, respectively.

Language: Английский

Citations

3
Chalcone Synthesis by Green Claisen–Schmidt Reaction in Cationic and Nonionic Micellar Media DOI Creative Commons

Davide Dotta,

Matteo Gastaldi, Andréa Fin

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 18, 2025

In this paper, micellar-mediated synthesis of chalcones was explored. After optimization the reaction conditions, cationic surfactant CTAB and nonionic one, Tween 80, were taken into consideration. Both surfactants used to study scope Claisen–Schmidt reactants, a wide on both aromatic aldehydes methyl ketones explored, obtaining from good very yields in most cases thus demonstrating that can be proficiently synthesized micellar solutions with functional group tolerability. Often, when one did not perform well, other performed better, use different constitute alternative overcome reactivity problems. Besides, 80 proposed as greener cases. Some reactions gave low yields, showing some specific improvements would needed address reactivity. The medium studied by NMR search for information about association reactants micelles their locations within them. Diffusion Ordered Spectroscopy (DOSY) applied assess interaction percentage incorporation micelles.

Language: Английский

Citations

0