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

Contemporary Approaches for Amide Bond Formation DOI
Paola Acosta‐Guzmán, Andrea Ojeda‐Porras, Diego Gamba‐Sánchez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4359 - 4391

Published: Nov. 7, 2023

Abstract Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out thirty‐seven new drugs approved by FDA 2022, eleven are small molecules containing at least amide bond. Additionally, there nineteen large as drugs, some which have peptide structures, and therefore, also bear bonds. In years, multiple teams embraced challenge developing more efficient methods for formation. This dedication led numerous publications appearing monthly prestigious journals, showcasing advancements this field. The primary goal review is present viable strategies constructing It crucial differentiate between formation synthesis; hence, focus on describing specific forming C(O)−N particular, concentrates developed within last six years. There a particular emphasis approaches that consider thought process when selecting starting materials groups. approach ensures coverage all common chemical transformations yield

Language: Английский

Citations

51
On the role of surfactants: rethinking “aqueous” chemistry DOI
Bruce H. Lipshutz

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(2), P. 739 - 752

Published: Dec. 11, 2023

Some of the latest technological developments involving chemistry in water are discussed.

Language: Английский

Citations

23
Nanoparticles as Heterogeneous Catalysts for ppm Pd-Catalyzed Aminations in Water DOI Creative Commons
Karthik S. Iyer,

Rahul D. Kavthe,

Yuting Hu

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(5), P. 1997 - 2008

Published: Jan. 22, 2024

A general protocol employing heterogeneous catalysis has been developed that enables ppm of Pd-catalyzed C-N cross-coupling reactions under aqueous micellar catalysis. new nanoparticle catalyst containing specifically ligated Pd, in combination with nanoreactors composed the designer surfactant Savie, a biodegradable amphiphile, catalyzes bond formations recyclable water. variety coupling partners, ranging from highly functionalized pharmaceutically relevant APIs to educts Merck Informer Library, readily participate these environmentally responsible, sustainable reaction conditions. Other key features associated this report include low levels residual Pd found products, recyclability medium, use ocean water as an alternative source options for pseudohalides and

Language: Английский

Citations

9
Facile, green, and functional group-tolerant reductions of carboxylic acids…in, or with, water DOI
Karthik S. Iyer, Chandler B. Nelson, Bruce H. Lipshutz

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2663 - 2671

Published: Jan. 1, 2023

Facile reductions of carboxylic acids to aldehydes or alcohols can be effected under mild conditions upon initial conversion their corresponding S -2-pyridyl thioesters.

Language: Английский

Citations

10
A focus on sustainable method development for greener synthesis DOI Creative Commons
Jasper L. Tyler, Felix Katzenburg, Frank Glorius

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(27), P. 7408 - 7410

Published: Jan. 1, 2023

Kavthe et al. ( Chem. Sci. , 2023, https://doi.org/10.1039/D3SC01699D) have demonstrated how employing more sustainable methodology can vastly reduce the environmental impact associated with synthesis of antimalarial drug candidate MMV688533.

Language: Английский

Citations

10
A Metallomicellar Catalyst for Controlled Oxidation of Alcohols and Lignin Mimics in Water using Open Air as Oxidant DOI
Prabaharan Thiruvengetam,

Pragyansmruti Sunani,

Dillip Kumar Chand

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(10)

Published: Jan. 15, 2024

Abstract Alcohol groups and β ‐O‐4 (C−C) linkages are widespread in biomass feedstock that abundant renewable resource for value‐added chemicals. The development of sustainable protocols direct oxidation or oxidative cleavage materials a controlled fashion, using open air as an oxidant is intellectually stimulating task to produce industrially important carbonyls. Further, the depolymerization lignin into fine chemicals has evoked interest recent times. Herein, we report first example catalyst system could activate molecular oxygen from atmospheric cleavage/depolymerization such alcohols, real water under conditions. selectivity carbonyl products by altering pH between ~7.0 ~12.0. current strategy highlights non‐involvement any external co‐catalyst, oxidant, radical additives, and/or destructive organic solvents. shows wide substrate scope eminent functional group tolerance. upscaled multigram synthesis inexpensive easily available evidences practical utility developed protocol. A plausible mechanism been proposed with help few experiments, kinetic computational studies.

Language: Английский

Citations

3
Dehydration in Water. Solid-Supported Lipases as Green Catalysts for Esterification DOI
Rohan M. Thomas,

Monica S. Lopez Lemus,

Krithika Ganesh

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(17), P. 9320 - 9329

Published: Jan. 1, 2024

Catalytic esterification in water has been achieved with the aid of a commercially available polymer-supported lipase, Novozym-435.

Language: Английский

Citations

3
The prospect of using polyvinyl chloride with -n-hydroxyl amine, a metal binding agent, to adsorb uranium from its aqueous solution DOI

Abd El-Hakeim T. Kandil,

Bahig M. Atia,

Farida El-Dars

et al.

Environmental Nanotechnology Monitoring & Management, Journal Year: 2025, Volume and Issue: unknown, P. 101055 - 101055

Published: Feb. 1, 2025

Language: Английский

Citations

0
A New Green Oxyma-Sulfonate Coupling Reagent for Sustainable Organic Transformations DOI
Sayanta Roy, Bhubaneswar Mandal

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Language: Английский

Citations

0
Flow-to-Flow Technology: Amide Formation in the Absence of Traditional Coupling Reagents Using DPDTC DOI Creative Commons

John M. Saunders,

Esveidy Oceguera Nava,

Jason Li

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: 13(18), P. 6646 - 6655

Published: April 29, 2025

Reported herein is the use of a recyclable coupling agent, 2,2'-dipyridyldithiocarbonate (DPDTC), that generates isolable thioesters in plug flow reactor (PFR). If not isolated, can be reintroduced directly into PFR, along with amines, to generate amides "flow-to-flow" sense. Both electron-rich and -poor aromatic acids, as well sterically hindered aliphatic are efficiently coupled variety including formation Weinreb peptides, high yields.

Language: Английский

Citations

0