{ "id": "epfqhp815b", "slug": "hydroamination", "title": "Hydroamination", "updated": "2026-10-15", "topic_path": [ { "id": "physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/topics/physical" }, { "id": "physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry" }, { "id": "physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods" }, { "id": "physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis" }, { "id": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis.named-preparative-methods" }, { "id": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-ho-to-z", "label": "Titles Ho to Z", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-ho-to-z" } ], "geo": [ { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Non-geographic · 1946 to 2000: Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "path": [ { "id": "geo.nongeo", "label": "Non-geographic", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo" }, { "id": "geo.nongeo.t1946", "label": "Non-geographic · 1946 to 2000", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946" }, { "id": "geo.nongeo.t1946.physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical" }, { "id": "geo.nongeo.t1946.physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods" } ] }, { "id": "geo.nongeo.t2001.physical.chemistry.methods.chemical-synthesis", "label": "Non-geographic · 2001 to 2020: Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001.physical.chemistry.methods.chemical-synthesis", "path": [ { "id": "geo.nongeo", "label": "Non-geographic", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo" }, { "id": "geo.nongeo.t2001", "label": "Non-geographic · 2001 to 2020", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001" }, { "id": "geo.nongeo.t2001.physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001.physical" }, { "id": "geo.nongeo.t2001.physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001.physical.chemistry" }, { "id": "geo.nongeo.t2001.physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001.physical.chemistry.methods" }, { "id": "geo.nongeo.t2001.physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t2001.physical.chemistry.methods.chemical-synthesis" } ] } ], "excerpt": "Hydroamination is the addition of an amine N–H bond across a carbon–carbon double or triple bond, forming a new C–N bond in one step with 100% theoretical atom economy.", "snippet": "Hydroamination is the addition of an amine N–H bond across a carbon–carbon double or triple bond, forming a new C–N bond in one step with 100% theoretical atom economy.", "node": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-ho-to-z", "markdown": "# Hydroamination\n\nHydroamination is the addition of an amine N–H bond across a carbon–carbon double or triple bond, forming a new C–N bond and a new C–H bond in a single step: alkenes give alkyl amines, and alkynes give enamines or imines.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Because every atom of both starting materials appears in the product, the reaction has a theoretical atom economy of 100%.[2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429)\n\n| Key fact | Detail |\n|---|---|\n| Products | Alkene hydroamination gives primary, secondary, or tertiary amines depending on the N–H substrate; alkynes give enamines and imines[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) |\n| Thermodynamics | NH₃ addition to ethene and ethyne is calculated at −9.8 and −17 kcal/mol; many alkene additions are near thermoneutral (ΔG° = −0.1 kcal/mol for diethylamine + 2-methyl-2-butene)[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) • [3](https://www.science.org/doi/10.1126/science.aal3010) |\n| Mechanistic manifolds | Amido insertion (early metals, lanthanides), imido [2+2] (Group 4), π-activation/nucleophilic attack or migratory insertion (late metals), radical aminium cation pathways[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) • [4](https://pubs.acs.org/doi/full/10.1021/acs.accounts.3c00141) |\n| Intramolecular vs intermolecular | Intermolecular reactions run ~350-fold (alkenes) and ~1400-fold (alkynes) slower[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) |\n| Representative performance | NiH/anthranil system: 72 examples, up to 97% yield and 99% ee[5](https://pubs.acs.org/accacs/article/15/19/16622/3692463/Regio-and-Enantioselective-Nickel-Catalyzed); Ir terminal-alkene system: TON 460, 93:7 e.r.[6](https://escholarship.org/content/qt7xs523v1/qt7xs523v1.pdf) |\n| Ammonia | Direct addition of NH₃ works for alkynes and allenes with gold catalysts but not yet for unactivated alkenes[7](https://pmc.ncbi.nlm.nih.gov/articles/PMC2529152/) • [8](https://www.nature.com/articles/s41586-020-2919-z) |\n\n## How it works\n\nThe uncatalyzed reaction is kinetically blocked: both the amine and the π-bond are electron-rich, and the barrier is raised by electrostatic repulsion between the nitrogen lone pair and the π-system and by an orbital-symmetry-forbidden [2+2] cycloaddition pathway.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) • [2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429) A further practical problem is catalyst poisoning: amines bind to metal centers, so moderately basic amines, amides, and cyclic ureas are often used instead of free alkylamines.[9](https://beta.iopscience.iop.org/article/10.1070/RCR4953)\n\nFour mechanistic families cover most systems.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Main-group, early-transition-metal, and rare-earth catalysts first form a metal–amido bond; the C–C multiple bond then inserts into that bond in the rate-determining step.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Group 4 metals operate through a metal imido complex that undergoes reversible [2+2] cycloaddition with an alkyne to an azametallacyclobutene, followed by rate-determining amine coordination and protonolysis.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Late transition metals instead activate the π-bond: for conjugated alkenes with Pd, Rh, Ni, or Ru the turnover-limiting step is nucleophilic attack of the amine on a coordinated benzyl, allyl, alkene, or arene ligand, whereas unconjugated alkenes with Ru and Ir react by turnover-limiting migratory insertion into a metal–nitrogen bond.[4](https://pubs.acs.org/doi/full/10.1021/acs.accounts.3c00141) Finally, photoredox methods oxidize the amine to an aminium radical cation; dialkyl aminium radical cations add to unactivated olefins with second-order rate constants above \\( 10^{8} \\) M⁻¹s⁻¹.[3](https://www.science.org/doi/10.1126/science.aal3010)\n\nFor unactivated alkenes the Markovnikov isomer usually predominates, and hydroamination of unactivated alkenes remains restricted to particular amine and catalyst combinations.[9](https://beta.iopscience.iop.org/article/10.1070/RCR4953) For alkynes, aliphatic amines tend to give anti-Markovnikov enamines while aromatic amines tend to give Markovnikov products.[9](https://beta.iopscience.iop.org/article/10.1070/RCR4953)\n\nAnti-Markovnikov placement is the harder target: it was named in 1993 as one of the 10 greatest challenges for catalysis research and remains highly challenging for unactivated alkenes and alkynes.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) An anti-Markovnikov product in terminal alkyne hydroamination was reported, using the titanium complex [(η⁵-Cp)₂Ti(η²-C₂(TMS)₂)] with tert-butylamine.[9](https://beta.iopscience.iop.org/article/10.1070/RCR4953)\n\n## How it is done\n\nRepresentative operating conditions show the practical spread. The Knowles photocatalytic protocol couples unactivated olefins with secondary alkyl amines at room temperature under blue LED irradiation.[3](https://www.science.org/doi/10.1126/science.aal3010) Cationic CAAC–gold(I) complexes add ammonia to unactivated alkynes and allenes with 5 mol% catalyst; 3-hexyne needed 160 °C for 3.5 h to give the primary imine cleanly.[7](https://pmc.ncbi.nlm.nih.gov/articles/PMC2529152/) For asymmetric work, an iridium precatalyst [Ir(S)-DTBM-SEGPHOS(Cl)] with an ethylene ligand and NaBArF hydroaminates unactivated terminal alkenes, giving 91% yield with 93:7 e.r..[6](https://escholarship.org/content/qt7xs523v1/qt7xs523v1.pdf) Nickel hydride protocols are run under argon in oven-dried screw-capped vials with NiBr₂·diglyme and a hydrosilane reductant, in solvent dried to below 20 ppm water.[5](https://pubs.acs.org/accacs/article/15/19/16622/3692463/Regio-and-Enantioselective-Nickel-Catalyzed)\n\n## Origin\n\nThe hydroamination in solution, the C,N coupling of p-toluidine with cyclohexene, is a known reaction.[2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429) Modern homogeneous catalysis began with the iridium(I)-catalyzed addition of aniline to norbornylene via N–H activation reported by Albert L. Casalnuovo, Joseph C. Calabrese, and [David Milstein](https://www.edgepedia.org/david-milstein) in 1988[10](https://doi.org/10.1021/ja00228a022), and with the organolanthanide-catalyzed intramolecular cyclization of unprotected amino olefins reported by [Michel R. Gagné](https://www.edgepedia.org/michel-r-gagne) and [Tobin J. Marks](https://www.edgepedia.org/tobin-j-marks) in 1989.[11](https://doi.org/10.1021/ja00193a056) The first intermolecular organolanthanide-catalyzed alkyne and alkene hydroaminations were reported by Yanwu Li and Tobin J. Marks in 1996.[12](https://doi.org/10.1021/om960293y) Motoi Kawatsura and John F. Hartwig reported palladium-catalyzed intermolecular hydroamination of vinylarenes with arylamines in 2000.[13](https://doi.org/10.1021/ja002284t) The field was framed by the reviews of Thomas E. Müller and Matthias Beller (1998)[14](https://doi.org/10.1021/cr960433d) and Thomas E. Müller and colleagues (2008).[15](https://doi.org/10.1021/cr0306788) Gold(I)-catalyzed alkene hydroaminations, intermolecular additions and intramolecular additions, both use Ph₃PAuOTf.[16](https://beilstein-journals.org/bjoc/content/pdf/1860-5397-20-43.pdf) • [17](https://doi.org/10.1021/ja053864z)\n\n## Variants\n\nIntramolecular hydroamination, cyclization of an aminoalkene or aminoalkyne, is far faster than the intermolecular reaction because it avoids the entropic penalty; intermolecular reactions of unactivated alkenes are the most challenging variant.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Intramolecular addition favors the Markovnikov product, giving α-alkyl N-heterocycles.[2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429)\n\nEnantioselective hydroamination developed from the [IrCl(diphosphine)]₂/fluoride system reported by Romano Dorta and colleagues in 1997.[18](https://doi.org/10.1021/ja972594k) Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines was reported by [Yang Yang](https://www.edgepedia.org/yang-yang) and colleagues in 2015[19](https://doi.org/10.1126/science.aab3753), and a cationic iridium system with a trimethylsilyl-substituted aryl phosphine and triflimide counteranion extended this to acyclic and cyclic internal alkenes with high enantioselectivity.[8](https://www.nature.com/articles/s41586-020-2919-z) Photoredox variants give anti-Markovnikov products: an organic photoredox system was reported by Tien M. Nguyen and [David A. Nicewicz](https://www.edgepedia.org/david-nicewicz) in 2013.[20](https://doi.org/10.1021/ja4031616) Related named transformations include [hydroaminoalkylation](https://www.edgepedia.org/hydroaminoalkylation), reported with tantalum–amidate complexes by Patrick Eisenberger and colleagues in 2009[21](https://doi.org/10.1002/anie.200903656) and with titanium catalysis by Raphael Kubiak, Insa Prochnow, and Sven Doye in 2008.[22](https://doi.org/10.1002/anie.200805169) A cooperative phosphine–photoredox catalyst system achieves Markovnikov hydroamination between N–H azoles and terminal, aliphatic alkenes[23](https://www.nature.com/articles/s41586-026-10263-7), and visible-light copper catalysis gives Markovnikov hydroamination with carbazoles, indoles, and aniline derivatives.[24](https://beilstein-journals.org/bjoc/content/pdf/1860-5397-22-73.pdf)\n\n## Applications\n\nA NiH-catalyzed regio- and enantioselective hydroamination of unactivated alkenes with anthranils delivers chiral amines in 72 examples with up to 97% yield and 99% ee.[5](https://pubs.acs.org/accacs/article/15/19/16622/3692463/Regio-and-Enantioselective-Nickel-Catalyzed) With the iridium terminal-alkene system, 0.2 mol% loading on a silyl-protected allylic alcohol gave over 1 g of chiral amine in 92% yield by simple filtration.[6](https://escholarship.org/content/qt7xs523v1/qt7xs523v1.pdf) Diynes with ammonia gave 2,5-disubstituted pyrroles in 87% and 96% yield.[7](https://pmc.ncbi.nlm.nih.gov/articles/PMC2529152/)\n\n## Limitations and alternatives\n\nHigh-yield, selective alkene hydroamination is difficult because the reactions often lack a thermodynamic driving force and are accompanied by alkene isomerization, telomerization, and oxidative amination.[4](https://pubs.acs.org/doi/full/10.1021/acs.accounts.3c00141) In enantioselective work, reversibility of the hydroamination has been shown to erode the enantiopurity of the products.[4](https://pubs.acs.org/doi/full/10.1021/acs.accounts.3c00141) Early-metal catalysts are less tolerant of polar functional groups and of air and moisture than late transition metal complexes.[2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429)\n\nFormal alternatives include hydroboration–electrophilic amination sequences, in which regioselectivity is set in the hydroboration step, and oxidation to an aldehyde followed by reductive amination.[1](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482) Aza-Wacker, Buchwald–Hartwig, aminoacetoxylation, and photoredox couplings are less atomically efficient than direct hydroamination.[2](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429) Copper catalysis offers an earth-abundant option with four mechanistic modes, though a CuBr₂/dppe/Ag system gave aniline products in only 14% yield.[24](https://beilstein-journals.org/bjoc/content/pdf/1860-5397-22-73.pdf) Heterogeneous catalysts, recoverable by simple centrifugation or filtration, are pursued for sustainability.[25](https://link.springer.com/article/10.1186/s13065-019-0606-7) Direct addition of ammonia itself to unactivated alkenes remains unsolved: ammonia hydroamination is demonstrated for alkynes and allenes with gold catalysts[7](https://pmc.ncbi.nlm.nih.gov/articles/PMC2529152/), or indirectly through a 2-amino-6-methylpyridine ammonia surrogate.[8](https://www.nature.com/articles/s41586-020-2919-z)\n\n## References\n\n1. [Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View (Escorihuela, Lledós, Ujaque, Chem. Rev. 2023)](https://www.chemrev.org/doi/10.1021/acs.chemrev.2c00482)\n2. [Jumping in the Chiral Pool: Asymmetric Hydroaminations with Early Metals (Molecules 2023, 28, 2702)](https://mdpi-res.com/d_attachment/molecules/molecules-28-02702/article_deploy/molecules-28-02702-v2.pdf?version=1679045429)\n3. [Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines (Science, 2017)](https://www.science.org/doi/10.1126/science.aal3010)\n4. [Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes (Ma & Hartwig, Acc. Chem. Res. 2023)](https://pubs.acs.org/doi/full/10.1021/acs.accounts.3c00141)\n5. [Regio- and Enantioselective Nickel-Catalyzed Hydroamination of Unactivated Alkenes with Anthranils (ACS Catalysis, 2025)](https://pubs.acs.org/accacs/article/15/19/16622/3692463/Regio-and-Enantioselective-Nickel-Catalyzed)\n6. [Enantioselective hydroamination of unactivated terminal alkenes (Science, eScholarship repository copy)](https://escholarship.org/content/qt7xs523v1/qt7xs523v1.pdf)\n7. [Homogeneous Catalytic Hydroamination of Alkynes and Allenes with Ammonia (Angewandte Chemie, PMC copy)](https://pmc.ncbi.nlm.nih.gov/articles/PMC2529152/)\n8. [Catalytic asymmetric addition of an amine N–H bond across internal alkenes (Nature, 2020)](https://www.nature.com/articles/s41586-020-2919-z)\n9. [Catalysis and regioselectivity in hydrofunctionalization reactions of unsaturated carbon bonds. Part II. Hydroamination (Russian Chemical Reviews)](https://beta.iopscience.iop.org/article/10.1070/RCR4953)\n10. [Albert L. Casalnuovo, Joseph C. Calabrese, David. Milstein (1988). Rational design in homogeneous catalysis. Iridium(I)-catalyzed addition of aniline to norbornylene via nitrogen-hydrogen activation. Journal of the American Chemical Society.](https://doi.org/10.1021/ja00228a022)\n11. [Michel R. Gagne, Tobin J. Marks (1989). Organolanthanide-catalyzed hydroamination. Facile, regiospecific cyclization of unprotected amino olefins. Journal of the American Chemical Society.](https://doi.org/10.1021/ja00193a056)\n12. [Yanwu Li, Tobin J. Marks (1996). Diverse Mechanistic Pathways and Selectivities in Organo-f-Element-Catalyzed Hydroamination. Intermolecular Organolanthanide-Catalyzed Alkyne and Alkene Hydroamination. Organometallics.](https://doi.org/10.1021/om960293y)\n13. [Motoi Kawatsura, John F. Hartwig (2000). Palladium-Catalyzed Intermolecular Hydroamination of Vinylarenes Using Arylamines. Journal of the American Chemical Society.](https://doi.org/10.1021/ja002284t)\n14. [Thomas E. Müller, Matthias Beller (1998). Metal-Initiated Amination of Alkenes and Alkynes. Chemical Reviews.](https://doi.org/10.1021/cr960433d)\n15. [Thomas E. Müller and colleagues (2008). Hydroamination: Direct Addition of Amines to Alkenes and Alkynes. Chemical Reviews.](https://doi.org/10.1021/cr0306788)\n16. [Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination (Beilstein J. Org. Chem.)](https://beilstein-journals.org/bjoc/content/pdf/1860-5397-20-43.pdf)\n17. [Junliang Zhang, Cai-Guang Yang, Chuan He (2006). Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins. Journal of the American Chemical Society.](https://doi.org/10.1021/ja053864z)\n18. [Romano Dorta and colleagues (1997). The [IrCl(Diphosphine)]2/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination. Journal of the American Chemical Society.](https://doi.org/10.1021/ja972594k)\n19. [Yang Yang and colleagues (2015). Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines. Science.](https://doi.org/10.1126/science.aab3753)\n20. [Tien M. Nguyen, David A. Nicewicz (2013). Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System. Journal of the American Chemical Society.](https://doi.org/10.1021/ja4031616)\n21. [Patrick Eisenberger and colleagues (2009). Tantalum–Amidate Complexes for the Hydroaminoalkylation of Secondary Amines: Enhanced Substrate Scope and Enantioselective Chiral Amine Synthesis. Angewandte Chemie International Edition.](https://doi.org/10.1002/anie.200903656)\n22. [Raphael Kubiak, Insa Prochnow, Sven Doye (2008). Titanium‐Catalyzed Hydroaminoalkylation of Alkenes by CH Bond Activation at sp3 Centers in the α‐Position to a Nitrogen Atom. Angewandte Chemie International Edition.](https://doi.org/10.1002/anie.200805169)\n23. [Markovnikov hydroamination of terminal alkenes by phosphine redox catalysis (Nature, 2026)](https://www.nature.com/articles/s41586-026-10263-7)\n24. [Recent advances in copper-catalyzed direct hydroamination of alkenes with (hetero)aromatic amines (Beilstein J. Org. Chem.)](https://beilstein-journals.org/bjoc/content/pdf/1860-5397-22-73.pdf)\n25. [A minireview of hydroamination catalysis: alkene and alkyne substrate selective, metal complex design (BMC Chemistry)](https://link.springer.com/article/10.1186/s13065-019-0606-7)\n\n---\n*Topic: Encyclopedia › Physical world and mathematics › Chemistry › Chemical principles and methods › Chemical synthesis › Named synthetic methods › Titles Ho to Z*\n\n*Initially written Sep 29, 2026 · Edited: Oct 15, 2026*\n\n*Copyright 2026 EdgeChat AI, a subsidiary of Biostate AI.*\n\nLicense: Edgepedia Community License 1.0, https://www.edgepedia.org/edgepedia/license\n", "same_as": [], "url": "https://www.edgepedia.org/hydroamination", "markdown_url": "https://www.edgepedia.org/hydroamination.md", "license": { "name": "Edgepedia Community License 1.0", "url": "https://www.edgepedia.org/edgepedia/license", "summary": "Free with credit, commercial use included. AI training is open to everyone. For other uses, organizations over USD 100M in revenue or 100M monthly users license separately.", "spdx": "LicenseRef-Edgepedia-Community-1.0" }, "credit": "\"Hydroamination\", Edgepedia (EdgeChat), https://www.edgepedia.org/hydroamination. Edgepedia Community License 1.0.", "credit_md": "\"[Hydroamination](https://www.edgepedia.org/hydroamination)\", Edgepedia (EdgeChat), [https://www.edgepedia.org/hydroamination](https://www.edgepedia.org/hydroamination). [Edgepedia Community License 1.0](https://www.edgepedia.org/edgepedia/license).", "credit_html": "\"Hydroamination\", Edgepedia (EdgeChat), https://www.edgepedia.org/hydroamination. Edgepedia Community License 1.0.", "speakable": "Hydroamination is the addition of an amine N–H bond across a carbon–carbon double or triple bond, forming a new C–N bond in one step with 100% theoretical atom economy." }