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Review
. 2019 Jul 11;13(1):89.
doi: 10.1186/s13065-019-0606-7. eCollection 2019 Dec.

A minireview of hydroamination catalysis: alkene and alkyne substrate selective, metal complex design

Jingpei Huo #  1 , Guozhang He  1 , Weilan Chen  1 , Xiaohong Hu  1 , Qianjun Deng  1 , Dongchu Chen #  1
Affiliations
Review

A minireview of hydroamination catalysis: alkene and alkyne substrate selective, metal complex design

Jingpei Huo et al. BMC Chem. .

Abstract

Organic compounds that contain nitrogen are very important intermediates in pharmaceutical and chemical industry. Hydroamination is the reaction that can form C-N bond with high atom economy. The research progress in metals catalyzed hydroamination of alkenes and alkynes from the perspective of reaction mechanism is categorized and summarized.

Keywords: Atom economy; C–N bond; Hydroamination; Metal catalysis.

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Conflict of interest statement

Competing interestsThe authors declare that they have no competing interests.

Figures

Scheme 1
Scheme 1
Addition of primary amines to cinnamyl alcohol
Scheme 2
Scheme 2
Rh-catalyzed hydroamination of primary aminoalkenes
Scheme 3
Scheme 3
The forming Rh complex intermediate state of hydroamination reaction
Scheme 4
Scheme 4
Hydroamination of 2,2-dimethylpent-4-enylamine catalyzed by (1,3-(SiMe3)2C9H5)Sc(CH2SiMe3)2(THF)
Scheme 5
Scheme 5
Hydroamination/cyclization of 1-(aminomethyl)-1-allylcyclohexane by Li2[(R)-C20H12N2-(C10H22)]
Scheme 6
Scheme 6
Hydroamination-cyclization of 1-(aminomethyl)-1-allylcyclohexane by {Li(THF)4}{Ln[(R)-C20H12N2(C10H22)]2}
Scheme 7
Scheme 7
Catalyzed cyclization of 2-aminohex-5-ene
Scheme 8
Scheme 8
Hydroamination reaction of terminal aminoalkenes and alkynes catalyzed by Ca catalyst
Scheme 9
Scheme 9
Reactions of thiols and amines with ethyl propiolate
Scheme 10
Scheme 10
Intermolecular hydroamination of monosubstituted allenes with secondary alkylamines catalyzed by a mixture of (dppf)PtCl2 and AgOTf in toluene at 80 °C
Scheme 11
Scheme 11
A mechanism for the platinum catalyzed hydroamination of allenes with secondary alkylamines
Scheme 12
Scheme 12
Rh-catalyzed hydroamination of styrene with piperidine
Scheme 13
Scheme 13
In situ catalyst screening of both primary and secondary aminoalkene substrates
Scheme 14
Scheme 14
Intramolecular hydroamination of amino olefins by FeCl3·6H2O
Scheme 15
Scheme 15
Hydroamination of amino olefins catalyzed by a mixture of [PtCl2(H2CdCH2)]2 and PPh3 in Dioxane at 120 °C
Scheme 16
Scheme 16
TpRh(C2H4)2/PPh3-catalyzed hydroamination of 1-octyne with amines
Scheme 17
Scheme 17
Cu(I)-catalyzed intramolecular hydroamination of aminoalkene
Scheme 18
Scheme 18
Asymmetric intermolecular hydroamination of 1-alkenes with a primary amine
Scheme 19
Scheme 19
Hydroamination of allenes with secondary alkylamines
Scheme 20
Scheme 20
Base-catalyzed hydroamination of styrene with l-(4-fluorophenyl)piperazine
Scheme 21
Scheme 21
Pd-catalyzed hydroamination of alkylamines with vinylarenes
Scheme 22
Scheme 22
Ruthenium-catalyzed hydroamination of vinylarenes with alkylamines
Scheme 23
Scheme 23
Synthesis of polysubstituted pyrroles from dialkyl ethylenecarboxylate and β-enamino ester
Scheme 24
Scheme 24
Photoinduced additions of azoles to 1-methyl-1-cyclohexene
Scheme 25
Scheme 25
The addition of alcohols and secondary amines by the cesium hydroxide and CsOH catalyzed in NMP
Scheme 26
Scheme 26
Pd-catalyzed hydroamination of styrene with aniline
Scheme 27
Scheme 27
One-pot synthesis of 1, 2, 5-three substituted pyrrole
Scheme 28
Scheme 28
A silver-catalyzed domino reaction of simple aniline and alkyne
Scheme 29
Scheme 29
Lewis acid catalyzed hydroamination of norbornene with aromatic amine
Scheme 30
Scheme 30
Au(I)/Zn(II)-catalyzed sequential intermolecular hydroamination reaction of 4-yne-nitriles with amine
Scheme 31
Scheme 31
Plausible mechanism for pyrrole formation by Au(I)/Zn(II)-catalyzed
Scheme 32
Scheme 32
Intermolecular hydroamination of unactivated alkenes and anilines catalyzed by lanthanide salts
See this image and copyright information in PMC

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