In organic chemistry, hydroamination is the addition of an N−H bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene.[1] In the ideal case, hydroamination is atom economical and green.[2] Amines are common in fine-chemical, pharmaceutical, and agricultural industries.[3][4][5][6] Hydroamination can be used intramolecularly to create heterocycles or intermolecularly with a separate amine and unsaturated compound. The development of catalysts for hydroamination remains an active area, especially for alkenes. Although practical hydroamination reactions can be effected for dienes and electrophilic alkenes, the term hydroamination often implies reactions metal-catalyzed processes.
^Togni, Antionio; Grützmacher, Hansjörg (2001). Catalytic heterofunctionalization: from hydroanimation to hydrozirconation (1. ed.). Weinheim: Wiley-VCH. doi:10.1002/3527600159. ISBN 978-3527302345.
^Beller, M.; Bolm, C. (2004). Transition metals for organic synthesis : building blocks and fine chemicals (2nd ed.). Weinheim: Wiley-VCH. doi:10.1002/9783527619405. ISBN 9783527306138.
^Reznichenko, A. L.; Hultszch, K. C. (2015). Hydroamination of Alkenes. Vol. 88. p. 1. doi:10.1002/0471264180.or088.01. ISBN 978-0471264187. {{cite book}}: |journal= ignored (help)
^Hultzsch, Kai C. (2005). "Catalytic asymmetric hydroamination of non-activated olefins". Org. Biomol. Chem. (Review). 3 (10): 1819–1824. doi:10.1039/b418521h. PMID 15889160.
^Hartwig, J. F. (2004). "Development of catalysts for the hydroamination of olefins" (PDF). Pure Appl. Chem.76 (3): 507–516. doi:10.1351/pac200476030507. S2CID 29945266.
^Pohlki, F.; Doye, S. (2003). "The catalytic hydroamination of alkynes". Chem. Soc. Rev.32 (2): 104–114. doi:10.1039/b200386b. PMID 12683107.
In organic chemistry, hydroamination is the addition of an N−H bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene...
solution, hydrogen gas and a heterogeneous metallic ruthenium catalyst. In hydroamination, amines add to alkenes. Alkylation, the addition of an alkyl group Acylation...
Ian J.; Hill, Michael S. (2005). "Calcium-Mediated Intramolecular Hydroamination Catalysis". Journal of the American Chemical Society. 127 (7): 2042–43...
involving alkylation of amines with alcohols, the byproduct being water. Hydroamination is another green method for N-alkylation. In the Menshutkin reaction...
significantly as dihydroxymethane. Conceptually similar reactions include hydroamination and hydroalkoxylation, which involve adding amines and alcohols to alkenes...
with an alkene to form a tertiary N-oxide. The reaction is a form of hydroamination and can be extended to the use of unsubstituted hydroxylamine, in which...
used industrially to produce tertiary amines such as tert-octylamine. Hydroamination of alkenes is also widely practiced. The reaction is catalyzed by zeolite-based...
hydrohalogenation haloalkanes free radicals mediated addition of hydrohalic acids Hydroamination amines addition of N−H bond across C−C double bond Hydroformylation...
transition metal catalysts which helps in catalysis of anti-Markovnikov hydroamination of alkenes. In one of her publications, she introduces a method to catalyze...
Joseph A. R. (1 January 2013). "Palladium catalyzed intermolecular hydroamination of 1-substituted allenes: an atom-economical method for the synthesis...
Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination". Angewandte Chemie International Edition. 57 (28): 8714–8718. doi:10...
for bark beetles. Myrcenol is obtained synthetically from myrcene via hydroamination of the 1,3-diene followed by hydrolysis and Pd-catalysed removal of...
the cationic palladium iPEPPSI complex shown above was used in the hydroamination of alkynes as well. The authors have demonstrated that the ligands actively...
Density and Precatalyst Selection in Group 2-Catalyzed Aminoalkene Hydroamination". Organometallics. 30 (6): 1493–1506. doi:10.1021/om101063m. Miyoshi...
Francine; Michon, Christophe (2014-08-01). "Asymmetric Intramolecular Hydroamination of Alkenes in Mild and Wet Conditions—Structure and Reactivity of Cationic...
organolanthanides in the catalytic intermolecular hydrophosphination and hydroamination of multiple C–C bonds". Dalton Transactions. 45 (48): 19172–19193. doi:10...
Williamson ether synthesis from alkyl halides and alkali metal alkoxides. Hydroamination Hydrofunctionalization Alonso, F., Beletskaya, I. P., Yus, M.,...
complete the catalytic cycle. Intramolecular hydroetherifications and hydroaminations proceed with anti-Markovnikov selectivity. One mechanism invokes the...
ligand, a gold-antimony complex can catalyze styrene polymerization and hydroamination after being activated by AgNTf2. Antimony Organoantimony chemistry Superacid...
of alkenes, carboalumination of alkenes, hydrosilylation of alkenes, hydroamination/cyclisation of alpha, omega-aminoalkenes and dimerisation of terminal...
Masahiro (2013-10-04). "Copper-Catalyzed Intermolecular Regioselective Hydroamination of Styrenes with Polymethylhydrosiloxane and Hydroxylamines". Angewandte...
October 2001). "η2-Alkynyl and Vinylidene Transition Metal Complexes. 7.1 Hydroamination of Neutral Tungsten−Vinylidene Complexes". Organometallics. 20 (23)...
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Prototypical intermolecular hydroamination reactions.
Examples of intramolecular hydroamination.
