Shows
The Cyclo EditionAsymmetric HydroaminationIn 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.
Musacch...2020-12-2136 minThe Cyclo EditionMark Levin InterviewIn 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.2020-12-0743 minThe Cyclo EditionDifluorinated Alkyl Bromide Synthesis via Chiral Iodoarene CatalysisIn 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.0c070432020-11-3030 minThe Cyclo EditionMarshall Brennan InterviewIn 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.2020-11-1653 minThe Cyclo EditionDaniele Leonori InterviewIn 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.2020-10-1936 minThe Cyclo EditionDehydrogenative Aniline SynthesisIn 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/s41586-020-2539-72020-10-1235 minThe Cyclo EditionM. Christina White InterviewIn 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.2020-09-2855 minThe Cyclo EditionLate-Stage C–H MethylationIn 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/s41586-020-2137-82020-09-2134 minThe Cyclo EditionTotal Synthesis of MaximiscinIn 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.0c032022020-09-0737 minThe Cyclo EditionPhotocatalytic DeracemizationIn 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.
2019-12-2333 minThe Cyclo EditionJake YestonIn this episode we interview Jake Yeston, who is Science's editor for physical sciences research. 2019-11-0445 minThe Cyclo EditionTotal Synthesis of PerseanolIn this episode we discuss the total synthesis of (+)-perseanol reported by the Reisman lab. The route proceeds in 16 steps and takes advantage of a convergent fragment coupling strategy.
DOI: https://doi.org/10.1038/s41586-019-1580-x2019-10-0723 minThe Cyclo EditionSilver-Catalysed Nitrene TransferIn this episode we interview the authors of a new paper on catalyst-controlled silver-catalysed nitrene transfer. By changing the ligand on silver the catalyst selectively functionalizes beta or gamma C-H bonds to form amino alcohols. Link: https://rdcu.be/bQGsf
2019-09-2326 minThe Cyclo EditionOrganocatalytic Mitsunobu ReactionsIn this episode we analyze a new paper from the Denton lab where they report a redox-neutral organocatalytic Mitsunobu reaction eliminating the need for stoichiometric, hazardous reagents.
DOI: 10.1126/science.aax3353
2019-09-0924 minThe Cyclo EditionThianthrenium Salts as New Synthetic LinchpinIn this episode we analyze a set of papers from the Ritter lab where they describe a new methodology for highly selective C–H functionalization reactions. Using thianthrenium salts as a synthetic linchpin, the Ritter lab demonstrates para selective amination, trifluoromethylation, and C–C cross-coupling reactions each in an effective two-step synthesis.2019-08-2621 minThe Cyclo EditionElectrophotocatalytic C-H OxidationIn this episode we analyze a paper from the Lambert lab where they report a new catalyst which upon electrochemical oxidation and photochemical excitation becomes a potent oxidant. The authors apply this strategy to coupling arenes and nitrogen heterocycles.
DOI: 10.1002/anie.201906381
2019-08-0518 minThe Cyclo EditionTotal Synthesis of ArcutinidineIn this episode we analyze the total synthesis of arcutinidine developed by the Li lab and compare it to recent syntheses completed by the Sarpong and Qin labs. 2019-07-2219 minThe Cyclo EditionDerivatizing Chiral Phosphorothioate SaltsIn this episode we discuss a new paper from the Schoenebeck lab where they report a new method to couple aryl iodides and chiral phosphorothioate salts using Pd(I) dimer catalysis. 2019-07-0823 minThe Cyclo EditionCleaving Olefins through HydrodealkenylationIn this episode we analyze a new paper from the Kwon lab where they report a deconstructive strategy to access chiral synthetic intermediates starting from terpene and terpenoid derived precursors.
DOI: 10.1126/science.aaw42122019-06-2424 minThe Cyclo EditionPhotochemical C-H Amination through in situ N-Chloroamines - LeonoriIn this episode we discuss a recent report from the Leonori lab on a new method for carbon-nitrogen bond formation by direct reaction of arenes and alkyl amines using photocatalysis. DOI: https://doi.org/10.1038/s41557-019-0254-5
2019-06-1025 minThe Cyclo EditionTrailerIntroducing The Cyclo Edition—the podcast for those looking to go above and beyond in their understanding of organic literature. Episodes will be released every other week starting June 10. 2019-05-2902 min