One-pot reductive amination of carbonyl compounds with ammonia via ‘hydrogen borrowing’ using hydrido- and bis-ammine P,O(Me)-ruthenacycles

Frederick P. Malan; Ji Hyang Noh; Gadada Naganagowda; Eric Singleton; Reinout Meijboom

doi:10.1016/j.jorganchem.2016.10.038

One-pot reductive amination of carbonyl compounds with ammonia via ‘hydrogen borrowing’ using hydrido- and bis-ammine P,O(Me)-ruthenacycles

Frederick P. Malan, Ji Hyang Noh, Gadada Naganagowda, Eric Singleton, Reinout Meijboom

Chemical Sciences

University of Johannesburg

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

The novel cationic [RuH{PPh₂(2-OMeC₆H₄)}₂]BPh₄and neutral trans-[Ru(NH₃)₂{PPh₂(2-OC₆H₄)}₂] complexes were isolated from phosphine substitution reactions with [RuH(1,5-cod)(NH₂NMe₂)₃]BPh₄and [RuCl(1,5-cod)(NH₃)₂(NH₂NMe₂)]BPh₄respectively. Ligand induced bisdemethylation of the pendent ether moieties of the phosphines occurred to give rise to the bis-phosphanylphenoxy moieties. Both complexes catalyzed the one-pot reductive amination of carbonyl compounds where excellent selectivity of aryl aldehydes over aryl ketones as precursors to the alcoholic species existed. Through substrate screening and¹H NMR studies, both steric and electronic effects of the substrates were found to influence the hydrogenation/amination mechanistic pathway, as well as direct the alcohol:amine selectivity.

Original language	English
Pages (from-to)	139-145
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	825-826
DOIs	https://doi.org/10.1016/j.jorganchem.2016.10.038
Publication status	Published - 2016

Keywords

Hemilability
Reductive amination
Ruthenium(II)
Transfer hydrogenation

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2016.10.038

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title = "One-pot reductive amination of carbonyl compounds with ammonia via {\textquoteleft}hydrogen borrowing{\textquoteright} using hydrido- and bis-ammine P,O(Me)-ruthenacycles",

abstract = "The novel cationic [RuH{PPh2(2-OMeC6H4)}2]BPh4and neutral trans-[Ru(NH3)2{PPh2(2-OC6H4)}2] complexes were isolated from phosphine substitution reactions with [RuH(1,5-cod)(NH2NMe2)3]BPh4and [RuCl(1,5-cod)(NH3)2(NH2NMe2)]BPh4respectively. Ligand induced bisdemethylation of the pendent ether moieties of the phosphines occurred to give rise to the bis-phosphanylphenoxy moieties. Both complexes catalyzed the one-pot reductive amination of carbonyl compounds where excellent selectivity of aryl aldehydes over aryl ketones as precursors to the alcoholic species existed. Through substrate screening and1H NMR studies, both steric and electronic effects of the substrates were found to influence the hydrogenation/amination mechanistic pathway, as well as direct the alcohol:amine selectivity.",

keywords = "Hemilability, Reductive amination, Ruthenium(II), Transfer hydrogenation",

author = "Malan, {Frederick P.} and Noh, {Ji Hyang} and Gadada Naganagowda and Eric Singleton and Reinout Meijboom",

note = "Publisher Copyright: {\textcopyright} 2016",

year = "2016",

doi = "10.1016/j.jorganchem.2016.10.038",

language = "English",

volume = "825-826",

pages = "139--145",

journal = "Journal of Organometallic Chemistry",

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T1 - One-pot reductive amination of carbonyl compounds with ammonia via ‘hydrogen borrowing’ using hydrido- and bis-ammine P,O(Me)-ruthenacycles

AU - Malan, Frederick P.

AU - Noh, Ji Hyang

AU - Naganagowda, Gadada

AU - Singleton, Eric

AU - Meijboom, Reinout

PY - 2016

Y1 - 2016

N2 - The novel cationic [RuH{PPh2(2-OMeC6H4)}2]BPh4and neutral trans-[Ru(NH3)2{PPh2(2-OC6H4)}2] complexes were isolated from phosphine substitution reactions with [RuH(1,5-cod)(NH2NMe2)3]BPh4and [RuCl(1,5-cod)(NH3)2(NH2NMe2)]BPh4respectively. Ligand induced bisdemethylation of the pendent ether moieties of the phosphines occurred to give rise to the bis-phosphanylphenoxy moieties. Both complexes catalyzed the one-pot reductive amination of carbonyl compounds where excellent selectivity of aryl aldehydes over aryl ketones as precursors to the alcoholic species existed. Through substrate screening and1H NMR studies, both steric and electronic effects of the substrates were found to influence the hydrogenation/amination mechanistic pathway, as well as direct the alcohol:amine selectivity.

AB - The novel cationic [RuH{PPh2(2-OMeC6H4)}2]BPh4and neutral trans-[Ru(NH3)2{PPh2(2-OC6H4)}2] complexes were isolated from phosphine substitution reactions with [RuH(1,5-cod)(NH2NMe2)3]BPh4and [RuCl(1,5-cod)(NH3)2(NH2NMe2)]BPh4respectively. Ligand induced bisdemethylation of the pendent ether moieties of the phosphines occurred to give rise to the bis-phosphanylphenoxy moieties. Both complexes catalyzed the one-pot reductive amination of carbonyl compounds where excellent selectivity of aryl aldehydes over aryl ketones as precursors to the alcoholic species existed. Through substrate screening and1H NMR studies, both steric and electronic effects of the substrates were found to influence the hydrogenation/amination mechanistic pathway, as well as direct the alcohol:amine selectivity.

KW - Hemilability

KW - Reductive amination

KW - Ruthenium(II)

KW - Transfer hydrogenation

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U2 - 10.1016/j.jorganchem.2016.10.038

DO - 10.1016/j.jorganchem.2016.10.038

M3 - Article

AN - SCOPUS:84994787754

SN - 0022-328X

VL - 825-826

SP - 139

EP - 145

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

One-pot reductive amination of carbonyl compounds with ammonia via ‘hydrogen borrowing’ using hydrido- and bis-ammine P,O(Me)-ruthenacycles

Abstract

Keywords

ASJC Scopus subject areas

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