Domino Hydrogenation−Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

 

Domino Hydrogenation−Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines
Org. Lett. 2015, 17, 3990−3993   DOI: 10.1021/acs.orglett.5b01842

 

Abstract Image

Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cyclohexylamines. This reaction works at rt for 12 h or at 60 °C under microwave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexylamines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h–1).

Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy
Laboratory of Green Synthetic Organic Chemistry, CEMIN − Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy
Org. Lett., 2015, 17 (16), pp 3990–3993
DOI: 10.1021/acs.orglett.5b01842
Publication Date (Web): July 31, 2015
Copyright © 2015 American Chemical Society

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b01842

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