Named Reactions Handbook & Quiz book
nrochemistry with lluis llorens

NROChemistry offers named reactions in organic chemistry with their mechanisms explained, step by step, easily, and entertainingly. It is a space for people interested in learning organic chemistry and the common named reactions chemists use in their labs every day.

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Named Reactions in Organic Chemistry

Named Reactions in Organic Chemistry
A saponification reaction. . Disclaimer: All chemical reactions demonstrated in this video are performed by trained professionals in a controlled laboratory environment. Do not attempt to replicate these experiments without appropriate training and supervision. Always use personal protective equipment (PPE) including lab coats, safety goggles, and gloves when handling chemicals. Be aware of the specific hazards associated with each chemical used, such as toxicity, flammability, and reactivity. For detailed information on each chemical refer to Material Safety Data Sheets (MSDS) or Safety Data Sheets (SDS). The creators of this video are not responsible for any harm or injury resulting from the misuse of the information provided. This video is for educational purposes only.
This video is about the first total syntheses of polycyclic diterpene phomopsene, which has been achieved using a unique cascade reorganization of carbon-carbon single bonds. The method involves: A novel Nazarov cyclization/double ring expansion developed by the authors, enabling rapid and stereospecific construction of the 5/5/5/5 tetraquinane scaffold with contiguous quaternary centers; and a one-pot strategic ring expansion through Beckmann fragmentation/recombination to efficiently assemble the required 5/5/6/5 tetracyclic skeleton of the target molecules. . Also in this video: 1,4-addition of the Grignard reagent and hydrolysis. CDI-mediated amide coupling. Formation of the cyclobutanone via enol triflate. Hornerβˆ’Wadsworthβˆ’Emmons reaction and hydrolysis. Formation of the Ξ²-ketoester. Condensation with cyclobutanone. Nazarov 4Ο€-conrotatory electrocyclization/double ring expansion. Krapcho decarboxylation. Allylic Rubottom-type oxidation. Protection of the alcohol with MOMCl. 1,4-reduction with sodium borohydride. Oximation with hydroxylamine. Beckmann fragmentation. DIBALH reduction of the nitrile. Cyclization on a neutral alumina column. Dessβˆ’Martin oxidation and double bond migration. Stereoselective installation of the methyl group. Removal of the MOM group under acidic conditions. Hydrogenation of the enone, followed by Dessβˆ’Martin oxidation. Selective protection of the carbonyl group on the six-membered ring. Oxidation of the ketone to the corresponding enone. 1,4-addition, oxidation, and hydrogenation sequence. Removal of the carbonyl group and deprotection. Radical bromination and elimination. Removal of the carbonyl group. . Reference: J. Am. Chem. Soc. 2023, 145, 21170βˆ’21175. https://doi.org/10.1021/jacs.3c07044
In this video I talk about the synthesis of incargranine A, an alkaloid that features a [2,2,2]-bicyclooctane core with six contiguous stereocenters. To synthesize this natural product, the authors took advantage of a previously proposed biosynthetic pathway from a hemiaminal intermediate. This pathway consists of a retro-oxa-Mannich, oxa-Michael, keto-enol tautomerization, and Mannich cascade. . Also in this video: Michael Addition: https://nrochemistry.com/michael-reaction/ Mannich Reaction: https://nrochemistry.com/mannich-reaction/ Buchwald-Hartwig Amination: https://nrochemistry.com/buchwald-hartwig-coupling/ . Reference: Angew. Chem. Int. Ed. 2023, e202314308. https://doi.org/10.1002/anie.202314308
In this video I talk about the synthesis of aberrarone, a natural product that bears a unique 6/5/5/5 tetracyclic ring system, four ketones, seven stereocenters, and three quaternary carbon centers. . For the synthesis of this diterpene, the authors envisioned the possibility of constructing the carboskeleton via a manganese-mediated intramolecular 5-exo/5-exo/5-exo radical cascade reaction. . Also in this video: Appel reaction: https://nrochemistry.com/appel-reaction/ Riley oxidation: https://nrochemistry.com/riley-oxidation/ . Reference: J. Am. Chem. Soc. 2023, 145, 9459. https://doi.org/10.1021/jacs.3c02511
I set up an oxidation reaction. In this transformation, I wanted to oxidize my primary alcohol to the corresponding aldehyde. One of the easiest and mildest ways to effect this transformation is through the action of Dess-Martin periodinane, DMP. Disclaimer: All chemical reactions demonstrated in this video are performed by trained professionals in a controlled laboratory environment. Do not attempt to replicate these experiments without appropriate training and supervision. Always use personal protective equipment (PPE) including lab coats, safety goggles, and gloves when handling chemicals. Be aware of the specific hazards associated with each chemical used, such as toxicity, flammability, and reactivity. For detailed information on each chemical refer to Material Safety Data Sheets (MSDS) or Safety Data Sheets (SDS). The creators of this video are not responsible for any harm or injury resulting from the misuse of the information provided. This video is for educational purposes only.
Adagrasib is a pharmaceutical approved by the FDA in 2022 for the treatment of non-small cell lung cancer. . Therapeutic area: oncology Disease: NSCLC Target: KRASG12C Mechanism of Action: Covalent inhibitor, allosteric inhibitor. RoA: PO Chemistry section: Retrosynthesis & Forward Synthesis . References: Mechanism of Action: 1. J Exp Clin Cancer Res 41, 27 (2022). https://doi.org/10.1186/s13046-021-02225-w 2. Science 351, 604-608 (2016). https://doi.org/10.1126/science.aad6204 3. NatureΒ 503, 548–551 (2013). https://www.nature.com/articles/nature12796 Synthesis: 1. Discovery route: J. Med. Chem. 2020, 63, 6679. Open access. https://doi.org/10.1021/acs.jmedchem.9b02052 2. Commercial route (Presented here): DOI: 10.26434/chemrxiv-2022-9b3s1. https://doi.org/10.26434/chemrxiv-2022-9b3s1 3. Improved route: Org. Lett. 2023, 25, 944. Open access. https://doi.org/10.1021/acs.orglett.2c04266 4. Deprotection with 2-mercaptoethanol: Org. Lett. 2022, 24, 3736. https://doi.org/10.1021/acs.orglett.2c01410
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Named Reactions by category

Oxidation

Reduction

Rearrangement

Cross-Coupling

Addition-Condensation

Substitution

Ring Formation

Elimination and Olefination

Homologation

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