Recent Advances in Nonprecious Metal Catalysis DOI
David J. Bernhardson, Eric C. Hansen, Aran K. Hubbell

et al.

Organic Process Research & Development, Journal Year: 2023, Volume and Issue: 27(11), P. 1913 - 1930

Published: Sept. 13, 2023

As the field of nonprecious metal catalysis continues to expand, we pursue a review series covering selected transformations in this area over short time interval highlight advancements. We seek raise awareness both current art and need continue development toward broader application or earth-abundant metals chemical pharmaceutical industries.

Language: Английский

ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation DOI Creative Commons
Jin Yang, Michelle C. Neary, Tianning Diao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(9), P. 6360 - 6368

Published: Feb. 23, 2024

Nickel-catalyzed Suzuki–Miyaura coupling (Ni-SMC) offers the potential to reduce cost of pharmaceutical process synthesis. However, its application has been restricted by challenges such as slow reaction rates, high catalyst loading, and a limited scope heterocycles. Despite recent investigations, mechanism transmetalation in Ni-SMC, often viewed turnover-limiting step, remains insufficiently understood. We elucidate "Ni-oxo" pathway, applying PPh2Me ligand, identify formation nickel-oxo intermediate step. Building on this insight, we develop scaffolding ProPhos, featuring pendant hydroxyl group connected phosphine via linker. The design preorganizes both nucleophile nickel catalyst, thereby facilitating transmetalation. This exhibits fast kinetics robust activity across wide range heteroarenes, with loading 0.5–3 mol %. For arene substrates, can be further reduced 0.1

Language: Английский

Citations

19
The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions DOI Creative Commons
Michael U. Luescher, Fabrice Gallou, Bruce H. Lipshutz

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(24), P. 9016 - 9025

Published: Jan. 1, 2024

Initial calculations of environmental footprints associated with using Ni vs Pd catalysis in a representative metal-catalyzed Suzuki–Miyaura cross-coupling reveal that the choice ligated metal is often NOT consequence. Rather, it culmination other parameters such as medium.

Language: Английский

Citations

17
Accelerating the Development of Sustainable Catalytic Processes through Data Science DOI
Jason M. Stevens, Jacob M. Ganley, Matthew J. Goldfogel

et al.

Organic Process Research & Development, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Language: Английский

Citations

1
Iridium-Induced Metal-Organic Framework Honeycomb Nanomaterials Catalysis: A Pathway to Boosting Hydrogen Evolution Reaction DOI
Rongfang Li, Xueyi Chen,

Z Bian

et al.

Journal of Alloys and Compounds, Journal Year: 2025, Volume and Issue: unknown, P. 179345 - 179345

Published: Feb. 1, 2025

Language: Английский

Citations

1
Base metal chemistry and catalysis DOI Creative Commons
Marissa L. Clapson, Connor S. Durfy, Devon Facchinato

et al.

Cell Reports Physical Science, Journal Year: 2023, Volume and Issue: 4(9), P. 101548 - 101548

Published: Aug. 21, 2023

This perspective provides an entry-level conversation concerning base metal catalysis as a green and sustainable solution in industrial academic contexts. We establish definition of "base metal," challenging readers to consider the ethical implications sourcing. explore what it means be "sustainable" provide information on current efforts synthetic chemistry. examples catalytic trends transformations popular fields such cross-coupling small-molecule conversion, highlighting relevant systems. Finally, we social context—for example, decisions related catalyst development are often driven by factors including costliness, safety, adoptability (whether society will accept its usage), performance. How do move forefront? Is concerned if materials fabricated from cheaper more abundant sources? does chemistry community guide this knowledge translation?

Language: Английский

Citations

15
General Method for Ni-Catalyzed C–N Cross-Couplings of (Hetero)Aryl Chlorides with Anilines and Aliphatic Amines under Homogeneous Conditions Using a Dual-Base Strategy DOI Open Access
Roberto Silva Villatoro,

Joshua R. Belfield,

Hadi D. Arman

et al.

Organometallics, Journal Year: 2023, Volume and Issue: 42(21), P. 3164 - 3172

Published: Nov. 1, 2023

A general method for the Ni-catalyzed Buchwald–Hartwig amination of (hetero)aryl chlorides using both anilines and aliphatic amines under homogeneous conditions has been developed. Key to success this is implementation a dual-base strategy that utilizes an amine base combined with soluble halide scavenger allows use single air-stable, commercially available Ni(II)-precatalyst phosphine ligand [(R,S)-Josiphos] combination promote aminations across broad scope pharmaceutically relevant nucleophiles at catalyst loadings as low 1.0 mol %.

Language: Английский

Citations

14
The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions DOI Creative Commons
Bruce H. Lipshutz, Fabrice Gallou, Michael U. Luescher

et al.

Published: Feb. 7, 2024

Substitution of one metal catalyst for another is not straightforward as simply justifying this change based on the availability and/or cost metals. A life cycle-like assessment was performed leading to conclusion that commonly held view use earth-abundant metals (and in case study, Ni) are replacements palladium most notably cross coupling reactions, and Suzuki-Miyaura couplings, particular, an incomplete analysis entire picture. This notion can be misleading, unfortunately derives nowadays mainly from standpoint cost, some degree, relative natural abundance mining impact each metal. However, a more realistic appreciation emerges when several additional reaction parameters involved couplings considered. Such unequivocally points major climate brought about by organic solvents, while actually play subordinate roles terms CO2-release into environment. Clearly, study reveals factors contribute various ways overall carbon footprint. Hence, far detailed required than typically being utilized!

Language: Английский

Citations

6
Better Together: Catalyzing Innovation in Organic Synthesis via Academic-Industrial Consortia DOI Open Access
Jesús Alcázar, Edward A. Anderson, Huw M. L. Davies

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(14), P. 2677 - 2681

Published: Jan. 29, 2024

ADVERTISEMENT RETURN TO ISSUEPREVEditorialNEXTBetter Together: Catalyzing Innovation in Organic Synthesis via Academic-Industrial ConsortiaJesús AlcázarJesús AlcázarGlobal Discovery Chemistry, Johnson & Innovative Medicine, Janssen-Cilag, S. A., Jarama 75 A, 45007 Toledo, SpainMore by Jesús Alcázarhttps://orcid.org/0000-0002-2726-196X, Edward A. AndersonEdward AndersonChemistry Research Laboratory, Department of University Oxford, 12 Mansfield Road, Oxford OX1 3TA, United KingdomMore Andersonhttps://orcid.org/0000-0002-4149-0494, Huw M. L. DaviesHuw DaviesDepartment Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, StatesMore Davieshttps://orcid.org/0000-0001-6254-9398, Rio FebrianRio FebrianDepartment Febrian, Christopher B. KellyChristopher KellyDiscovery Process Research, 1400 McKean Spring House, Pennsylvania 19477, Kellyhttps://orcid.org/0000-0002-5530-8606, Timothy NoëlTimothy NoëlFlow Chemistry Group, van't Hoff Institute for Molecular Sciences (HIMS), Amsterdam, 1098 XH The NetherlandsMore Noëlhttps://orcid.org/0000-0002-3107-6927, Eric VoightEric VoightDiscovery AbbVie, Inc., 1 N Waukegan Rd, North Chicago, Illinois 60064, Voighthttps://orcid.org/0000-0002-9542-5356, Cayetana Zarate*Cayetana ZarateChemical R&D, Janssen-Cilag AG, Hochstrasse 201, 8200 Schaffhausen, Switzerland*Email: [email protected]More Zaratehttps://orcid.org/0000-0002-4002-6147, and Eli Zysman-ColmanEli Zysman-ColmanOrganic Semiconductor Centre, EaStCHEM School St Andrews, Haugh, KY16 9ST U.K.More Zysman-Colmanhttps://orcid.org/0000-0001-7183-6022Cite this: Org. Lett. 2024, 26, 14, 2677–2681Publication Date (Web):January 29, 2024Publication History Received17 January 2024Published online29 inissue April 2024https://pubs.acs.org/doi/10.1021/acs.orglett.4c00192https://doi.org/10.1021/acs.orglett.4c00192editorialACS PublicationsCopyright © Published 2024 American Chemical Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views5626Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (2 MB) Get e-Alertsclose e-Alerts

Language: Английский

Citations

5
Diversification of Pharmaceutical Manufacturing Processes: Taking the Plunge into the Non-PGM Catalyst Pool DOI Creative Commons
Hui Zhao, Anne K. Ravn, Michael C. Haibach

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(13), P. 9708 - 9733

Published: June 13, 2024

Recent global events have led to the cost of platinum group metals (PGMs) reaching unprecedented heights. Many chemical companies are therefore starting seriously consider and evaluate if where they can substitute PGMs for non-PGMs in their catalytic processes. This review covers recent highly relevant applications non-PGM catalysts modern pharmaceutical industry. By highlighting these selected successful examples non-PGM-catalyzed processes from literature, we hope emphasize enormous potential catalysis inspire further development within this field enable technology progress toward manufacturing We also present some historical contexts perceived advantages challenges implementing environment.

Language: Английский

Citations

5
Noble Metal versus Abundant Metal Catalysts in Fine Organic Synthesis: Cost Comparison of C–H Activation Methods DOI
Alina A. Komarova, Dmitry S. Perekalin

Organometallics, Journal Year: 2023, Volume and Issue: 42(13), P. 1433 - 1438

Published: June 23, 2023

There is a common assumption that replacement of the classical catalyst based on rare and expensive noble metals by catalysts earth-abundant will dramatically reduce costs organic synthesis. Herein we demonstrate it may not be true, mainly because sophisticated substrates modern reagents are often as catalytic amounts metals. The particular cost analysis syntheses 3,4-diphenyl-isoquinolone various C–H activation methods revealed main fall stoichiometric rather than catalysts. As result, metal-free synthesis appears to even more procedures involving ruthenium rhodium Overall, metal prices should considered sole reason for conducting academic research without any preliminary analysis.

Language: Английский

Citations

10