Podcast
The Cyclo Edition
Hosted by Matthew Genzink · EN
The Cyclo Edition is the podcast for those looking to go above and beyond in their understanding of organic chemistry literature. In each episode we break down a recently published paper and detail the background, explain the breakthrough, and analyze the broader impacts of the paper on the field.
10episodes
Episodes
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Asymmetric Hydroamination
Dec 21, 202000:36:01Tap to summarizeIn this episode we discuss a report from the Hartwig lab on an enantioselective hydroamination reaction. Through rational catalyst design, a cationic iridium complex was discovered that adds an amine N–H bond across a range of unactivated, internal alkenes. DOI: 10.1038/s41586-020-2919-z Xi, Y.; Ma, S.; Hartwig, J. F. Catalytic asymmetric addition of an amine N–H bond across internal alkenes. Nature 2020. Nguyen, T. M.; Manohar, N.; Nicewicz, D. A. anti-Markovnikov Hydroamination of Alkenes Catalyzed by a Two-Component Organic Photoredox System: Direct Access to Phenethylamine Derivatives. Angew. Chem. Int. Ed. 2014, 53, 6198–6201. Musacchio, A. J.; Lainhart, B. C.; Zhang, X.; Naguib, S. G.; Sherwood, T. C.; Knowles, R. R. Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines. Science, 2017, 355, 727–730. Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Late Transition Metal-Catalyzed Hydroamination and Hydroamidation. Chem. Rev. 2015, 115, 2596–2697. Gurak, J. A.; Yang, K. S.; Liu, Z.; Engle, K. M. Directed, Regiocontrolled Hydroamination of Unactivated via Protodepalladation. J. Am. Chem. Soc. 2016, 138, 5805–5808. Vanable, E. P.; Kennemur, J. L.; Joyce, L. A.; Ruck, R. T.; Schultz, D. M.; Hull, K. L. Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines. J. Am. Chem. Soc. 2019, 141, 739–742. Zhang, J.; Yang, C.-G.; He, C. Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins. J. Am. Chem. Soc. 2006, 128, 1798–1799. Zhang, Z.; Lee, S. D.; Widenhoefer, R. A. Intermolecular Hydroamination of Ethylene and 1-Alkenes with Cyclic Ureas Catalyzed by Achiral and Chiral Gold(I) Complexes. J. Am. Chem. Soc. 2009, 131, 5372– 5373. Zhou, J.; Hartwig, J. F. Intermolecular, Catalytic Asymmetric Hydroamination of Bicyclic Alkenes and Dienes in High Yield and Enantioselectivity. J. Am. Chem. Soc. 2008, 130, 12220–12221. Sevov, C. S.; Zhou, J.; Hartwig, J. F. Iridium-Catalyzed Intermolecular Hydroamination of Unactivated Aliphatic Alkenes with Amides and Sulfonamides. J. Am. Chem. Soc. 2012, 134, 11960–11963. Hanley, P. S.; Hartwig, J. F. Intermolecular Migratory Insertion of Unactivated Olefins into Palladium-Nitrogen Bonds. Steric and Electronic Effects on the Rate of Migratory Insertion. J. Am. Chem. Soc. 2011, 133, 15661–15673. Pan, S.; Endo, K.; Shibata, T. Ir(I)-Catalyzed Intermolecular Regio- and Enantioselective Hydroamination of Alkenes with Heteroaromatic Amines. Org. Lett. 2012, 14, 780–783. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Rational design in homogeneous catalysis. Iridium(I)-catalyzed addition of aniline to norbornylene via nitrogen-hydrogen activation. J. Am. Chem. Soc. 1988, 110, 6738–6744.
Transcribe →Mark Levin Interview
Dec 7, 202000:43:52Tap to summarizeIn this episode we interview Mark Levin, an Assistant Professor at UChicago. We discuss his recent publication with the Jacobsen group, life as a new professor, and places to eat in Chicago.
Transcribe →Difluorinated Alkyl Bromide Synthesis via Chiral Iodoarene Catalysis
Nov 30, 202000:30:11Tap to summarizeIn this episode we discuss a report from the Jacobsen lab on an enantioselective synthesis of difluorinated alkyl bromides catalyzed by a chiral iodoarene. Linear free energy relationships between experimental enantioselectivities and computed catalyst parameters helped elucidate the origins of enantioselectivity. DOI: 10.1021/jacs.0c07043
Transcribe →Marshall Brennan Interview
Nov 16, 202000:53:35Tap to summarizeIn this episode we interview Marshall Brennan, the founder and Senior Product Manager of ChemRxiv. We discuss open-access publishing, alternative chemistry careers, and much more.
Transcribe →Daniele Leonori Interview
Oct 19, 202000:36:41Tap to summarizeIn this episode we interview Dr. Daniele Leonori, who is a professor of chemistry at the University of Manchester. We discuss his recent paper on dehydrogenative aniline synthesis, differences between the UK and US academic system, and much more.
Transcribe →Dehydrogenative Aniline Synthesis
Oct 12, 202000:35:29Tap to summarizeIn this episode we discuss a report from the Leonori lab on a photochemical dehydrogenative strategy for aniline synthesis. Photoredox and cobalt catalysis are combined to transform cyclohexanones into anilines. DOI: 10.1038/s41586-020-2539-7
Transcribe →M. Christina White Interview
Sep 28, 202000:55:22Tap to summarizeIn this episode we interview Dr. M. Christina White, who is a professor of chemistry at the University of Illinois. We discuss her recent paper on C–H methylation as well as her program on site-selective C–H oxidation chemistry.
Transcribe →Late-Stage C–H Methylation
Sep 21, 202000:34:54Tap to summarizeIn this episode we discuss a report from the White lab on a new method for late-stage C–H methylation adjacent to heteroatoms. DOI: 10.1038/s41586-020-2137-8
Transcribe →Total Synthesis of Maximiscin
Sep 7, 202000:37:20Tap to summarizeIn this episode we discuss the total synthesis of (–)-maximiscin reported by the Baran lab. The route takes advantage of a convergent fragment coupling strategy with a late-stage formation of the central pyridone ring. DOI: https://doi.org/10.1021/jacs.0c03202
Transcribe →Photocatalytic Deracemization
Dec 23, 201900:33:56Tap to summarizeIn this episode we discuss a report from the Knowles lab on a method for catalytic deracemization using visible light. This strategy benefits from two independent stereoselective steps resulting in a highly enantioselective transformation. DOI: 10.1126/science.aay2204.
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