Herein, we broaden the application scope of (cyclopentadienone) iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Knölker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.

Improving C=N Bond Reductions with (Cyclopentadienone)iron Complexes: Scope and Limitations / M. Cettolin, X. Bai, D. Lübken, M. Gatti, S. Vailati Facchini, U. Piarulli, L. Pignataro, C. Gennari. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2019:4(2019 Jan 31), pp. 647-654. [10.1002/ejoc.201801348]

Improving C=N Bond Reductions with (Cyclopentadienone)iron Complexes: Scope and Limitations

M. Cettolin
Primo
;
X. Bai
Secondo
;
L. Pignataro
Penultimo
;
C. Gennari
Ultimo
2019-01-31

Abstract

Herein, we broaden the application scope of (cyclopentadienone) iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Knölker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
Transfer hydrogenation; Iron; Amination; Imines; Asymmetric catalysis
Settore CHIM/06 - Chimica Organica
PIANO DI SOSTEGNO ALLA RICERCA 2015-2017 - LINEA 2 "DOTAZIONE ANNUALE PER ATTIVITA' ISTITUZIONALE"
13-set-2018
Article (author)
File in questo prodotto:
File Dimensione Formato  
Piarulli_Pignataro_Gennari_EuJOC_2019_647.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 1.3 MB
Formato Adobe PDF
1.3 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Piarulli_Pignataro_Gennari_EurJOC_2019_647_Post-print.pdf

embargo fino al 06/05/2020

Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 825.28 kB
Formato Adobe PDF
825.28 kB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/595087
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 13
social impact