David MacMillan
Princeton University
H-index: 125
North America-United States
Description
David MacMillan, With an exceptional h-index of 125 and a recent h-index of 85 (since 2020), a distinguished researcher at Princeton University, specializes in the field of organic chemistry.
His recent articles reflect a diverse array of research interests and contributions to the field:
Direct Bioisostere Replacement Enabled by Metallaphotoredox Deoxydifluoromethylation
Current advances in photocatalytic proximity labeling
Alkene dialkylation by triple radical sorting
Couple-close construction of polycyclic rings from diradicals
Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis
Sustainable Synthesis via Novel Activation Modes: Organocatalysis and Photoredox Catalysis
Alcohol-alcohol cross-coupling enabled by SH2 radical sorting
Discussions of Session 1—Catalysis for Sustainable Chemistry
Professor Information
University | Princeton University |
---|---|
Position | ___ |
Citations(all) | 70531 |
Citations(since 2020) | 33811 |
Cited By | 49244 |
hIndex(all) | 125 |
hIndex(since 2020) | 85 |
i10Index(all) | 243 |
i10Index(since 2020) | 225 |
University Profile Page | Princeton University |
Research & Interests List
organic chemistry
Top articles of David MacMillan
Direct Bioisostere Replacement Enabled by Metallaphotoredox Deoxydifluoromethylation
The replacement of a functional group with its corresponding bioisostere is a widely employed tactic during drug discovery campaigns that allows medicinal chemists to improve the ADME properties of candidates while maintaining potency. However, the incorporation of bioisosteres typically requires lengthy de novo resynthesis of potential candidates, which represents a bottleneck in their broader evaluation. An alternative would be to directly convert a functional group into its corresponding bioisostere at a late stage. Herein, we report the realization of this approach through the conversion of aliphatic alcohols into the corresponding difluoromethylated analogues via the merger of benzoxazolium-mediated deoxygenation and copper-mediated C(sp3)–CF2H bond formation. The utility of this method is showcased in a variety of complex alcohols and drug compounds.
Authors
Edna Mao,Cesar N Prieto Kullmer,Holt A Sakai,David WC MacMillan
Journal
Journal of the American Chemical Society
Published Date
2024/2/16
Current advances in photocatalytic proximity labeling
Understanding the intricate network of biomolecular interactions that govern cellular processes is a fundamental pursuit in biology. Over the past decade, photocatalytic proximity labeling has emerged as one of the most powerful and versatile techniques for studying these interactions as well as uncovering subcellular trafficking patterns, drug mechanisms of action, and basic cellular physiology. In this article, we review the basic principles, methodologies, and applications of photocatalytic proximity labeling as well as examine its modern development into currently available platforms. We also discuss recent key studies that have successfully leveraged these technologies and importantly highlight current challenges faced by the field. Together, this review seeks to underscore the potential of photocatalysis in proximity labeling for enhancing our understanding of cell biology while also providing perspective on …
Authors
Steve D Knutson,Benito F Buksh,Sean W Huth,Danielle C Morgan,David WC MacMillan
Published Date
2024/4/12
Alkene dialkylation by triple radical sorting
The development of bimolecular homolytic substitution (SH2) catalysis has expanded cross-coupling chemistries by enabling the selective combination of any primary radical with any secondary or tertiary radical via a radical sorting mechanism1–8. Biomimetic9,10 SH2 catalysis can be used to merge common feedstock chemicals—such as alcohols, acids, and halides—in various permutations for the construction of a single C(sp3)–C(sp3) bond. The ability to sort these two distinct radicals across commercially available alkenes in a three-component manner would enable the simultaneous construction of two C(sp3)–C(sp3) bonds, greatly accelerating access to complex molecules and drug-like chemical space11. However, the simultaneous in situ formation of electrophilic and primary nucleophilic radicals in the presence of unactivated alkenes is problematic, typically leading to statistical radical recombination …
Authors
Johnny Z Wang,William L Lyon,David WC MacMillan
Journal
Nature
Published Date
2024/2/13
Couple-close construction of polycyclic rings from diradicals
Heteroarenes are ubiquitous motifs in bioactive molecules, conferring favourable physical properties when compared to their arene counterparts 1, 2, 3. In particular, semisaturated heteroarenes possess attractive solubility properties and a higher fraction of sp 3 carbons, which can improve binding affinity and specificity. However, these desirable structures remain rare owing to limitations in current synthetic methods 4, 5, 6. Indeed, semisaturated heterocycles are laboriously prepared by means of non-modular fit-for-purpose syntheses, which decrease throughput, limit chemical diversity and preclude their inclusion in many hit-to-lead campaigns 7, 8, 9, 10. Herein, we describe a more intuitive and modular couple-close approach to build semisaturated ring systems from dual radical precursors. This platform merges metallaphotoredox C (sp 2)–C (sp 3) cross-coupling with intramolecular Minisci-type radical …
Authors
Alice Long,Christian J Oswood,Christopher B Kelly,Marian C Bryan,David WC MacMillan
Journal
Nature
Published Date
2024/4
Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis
Although alcohols are among the most abundant chemical feedstock, they remain vastly underutilized as coupling partners in transition metal catalysis. Herein, we describe a copper metallaphotoredox manifold for an open shell deoxygenative coupling of alcohols with N-nucleophiles forging C(sp3)–N bonds, a linkage highly sought in pharmaceutical agents but challenging to access via conventional cross-coupling techniques. N-heterocyclic carbene (NHC)-mediated conversion of alcohols into the corresponding alkyl radicals followed by copper-catalyzed C–N coupling renders this platform successful for a broad range of structurally unbiassed alcohols and 18 classes of N-nucleophiles.
Authors
William P Carson II,Artem V Tsymbal,Robert W Pipal,Grant A Edwards,Joseph R Martinelli,Albert Cabré,David WC MacMillan
Published Date
2024/2/2
Sustainable Synthesis via Novel Activation Modes: Organocatalysis and Photoredox Catalysis
Catalysis impacts society broadly, enabling advancements in diverse areas that range from renewable energy to drug discovery. Indeed, around 35% of gross domestic product (GDP) globally relies on catalysis [1], and over 75% of all industrial chemical transformations and 90% of newly developed processes utilize catalysts [2]. Due to the ubiquitous and essential nature of catalysis, the development of more efficient and environmentally friendly catalytic processes represents a key step towards a more sustainable future.Within chemical industry, the pharmaceutical and fine chemical sector is a particularly crucial area for the implementation of sustainable catalysis. Pharmaceutical and fine chemical synthesis is currently reliant on non-sustainable technologies, such as precious metal catalysis [3], and this sector generates over an order of magnitude more waste per product
Authors
Colin A Gould,David WC MacMillan
Published Date
2024
Alcohol-alcohol cross-coupling enabled by SH2 radical sorting
Alcohols represent a functional group class with unparalleled abundance and structural diversity. In an era of chemical synthesis that prioritizes reducing time to target and maximizing exploration of chemical space, harnessing these building blocks for carbon-carbon bond-forming reactions is a key goal in organic chemistry. In particular, leveraging a single activation mode to form a new C(sp3)–C(sp3) bond from two alcohol subunits would enable access to an extraordinary level of structural diversity. In this work, we report a nickel radical sorting–mediated cross-alcohol coupling wherein two alcohol fragments are deoxygenated and coupled in one reaction vessel, open to air.
Authors
Ruizhe Chen,Nicholas E Intermaggio,Jiaxin Xie,James A Rossi-Ashton,Colin A Gould,Robert T Martin,Jesús Alcázar,David WC MacMillan
Journal
Science
Published Date
2024/3/22
Discussions of Session 1—Catalysis for Sustainable Chemistry
Thank you everyone for your participation this morning. I was asked by Kurt Wüthrich to make a quick note of something which I think is important. Originally, this first session was supposed to be chaired by Bob Grubbs, who unfortunately passed away in December of 2021. He was a person who attended this meeting many times. He was a wonderful guy, and he was the person who actually came up with this concept of sustainable catalysis. That was the reason we led off with it and I just wanted to remind everyone of that and what a really wonderful and fantastic guy Bob was. So now I think we’ll get started on the discussion. Maybe we could lead off with some questions to put to the panel and also to the group. The first one I wanted to start off with, when we’re talking about sustainable catalysis, is about performing chemical processes on scale.
Authors
David MacMillan,C Theunissen,F Tielens
Published Date
2024
Professor FAQs
What is David MacMillan's h-index at Princeton University?
The h-index of David MacMillan has been 85 since 2020 and 125 in total.
What are David MacMillan's top articles?
The articles with the titles of
Direct Bioisostere Replacement Enabled by Metallaphotoredox Deoxydifluoromethylation
Current advances in photocatalytic proximity labeling
Alkene dialkylation by triple radical sorting
Couple-close construction of polycyclic rings from diradicals
Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis
Sustainable Synthesis via Novel Activation Modes: Organocatalysis and Photoredox Catalysis
Alcohol-alcohol cross-coupling enabled by SH2 radical sorting
Discussions of Session 1—Catalysis for Sustainable Chemistry
...
are the top articles of David MacMillan at Princeton University.
What are David MacMillan's research interests?
The research interests of David MacMillan are: organic chemistry
What is David MacMillan's total number of citations?
David MacMillan has 70,531 citations in total.