Heterogeneously catalyzed selective hydrogenation of amides to alcohols and amines

Yinjun Xie; Peng Hu; Tatyana Bendikov; David Milstein

doi:10.1039/c8cy00112j

Heterogeneously catalyzed selective hydrogenation of amides to alcohols and amines

Yinjun Xie, Peng Hu, Tatyana Bendikov, David Milstein

Weizmann Institute of Science, Israel

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

10 Citations (Scopus)

Abstract

We report the heterogeneously catalyzed hydrogenation of amides to form alcohols and amines. This C-N bond cleavage reaction is catalyzed by silver on γ-alumina, proceeds smoothly in high yields and 100% selectivity, and is effective for both benzamides and aliphatic amides. This is in contrast to amide hydrogenation catalyzed by heterogeneous catalysts, which generally proceeds via C-O bond cleavage. Recycling experiments show that the catalyst Ag/γ-Al₂O₃ can be easily recovered and regenerated without decrease in catalytic activity.

Original language	English
Pages (from-to)	2784-2788
Number of pages	5
Journal	Catalysis Science and Technology
Volume	8
Issue number	11
DOIs	https://doi.org/10.1039/c8cy00112j
Publication status	Published - 2018

ASJC Scopus subject areas

Catalysis

Access to Document

10.1039/c8cy00112j

Fingerprint Dive into the research topics of 'Heterogeneously catalyzed selective hydrogenation of amides to alcohols and amines'. Together they form a unique fingerprint.

Cite this

@article{c96c86d9c2ed4ba19556770aeab63e19,

title = "Heterogeneously catalyzed selective hydrogenation of amides to alcohols and amines",

abstract = "We report the heterogeneously catalyzed hydrogenation of amides to form alcohols and amines. This C-N bond cleavage reaction is catalyzed by silver on γ-alumina, proceeds smoothly in high yields and 100% selectivity, and is effective for both benzamides and aliphatic amides. This is in contrast to amide hydrogenation catalyzed by heterogeneous catalysts, which generally proceeds via C-O bond cleavage. Recycling experiments show that the catalyst Ag/γ-Al2O3 can be easily recovered and regenerated without decrease in catalytic activity.",

author = "Yinjun Xie and Peng Hu and Tatyana Bendikov and David Milstein",

note = "Funding Information: This research was supported by the European Research Council (ERC AdG 692775). D. M. holds the Israel Matz Professorial Chair of Organic Chemistry. Y. X. thanks the Alternative Sustainable Energy Research Initiative (AERI) of the Weizmann Institute for a postdoctoral fellowship. We thank Dr. Yishay Feldman for help with XRD analysis.",

year = "2018",

doi = "10.1039/c8cy00112j",

language = "English",

volume = "8",

pages = "2784--2788",

journal = "Catalysis Science and Technology",

issn = "2044-4753",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Heterogeneously catalyzed selective hydrogenation of amides to alcohols and amines

AU - Xie, Yinjun

AU - Hu, Peng

AU - Bendikov, Tatyana

AU - Milstein, David

N1 - Funding Information: This research was supported by the European Research Council (ERC AdG 692775). D. M. holds the Israel Matz Professorial Chair of Organic Chemistry. Y. X. thanks the Alternative Sustainable Energy Research Initiative (AERI) of the Weizmann Institute for a postdoctoral fellowship. We thank Dr. Yishay Feldman for help with XRD analysis.

PY - 2018

Y1 - 2018

N2 - We report the heterogeneously catalyzed hydrogenation of amides to form alcohols and amines. This C-N bond cleavage reaction is catalyzed by silver on γ-alumina, proceeds smoothly in high yields and 100% selectivity, and is effective for both benzamides and aliphatic amides. This is in contrast to amide hydrogenation catalyzed by heterogeneous catalysts, which generally proceeds via C-O bond cleavage. Recycling experiments show that the catalyst Ag/γ-Al2O3 can be easily recovered and regenerated without decrease in catalytic activity.

AB - We report the heterogeneously catalyzed hydrogenation of amides to form alcohols and amines. This C-N bond cleavage reaction is catalyzed by silver on γ-alumina, proceeds smoothly in high yields and 100% selectivity, and is effective for both benzamides and aliphatic amides. This is in contrast to amide hydrogenation catalyzed by heterogeneous catalysts, which generally proceeds via C-O bond cleavage. Recycling experiments show that the catalyst Ag/γ-Al2O3 can be easily recovered and regenerated without decrease in catalytic activity.

UR - http://www.scopus.com/inward/record.url?scp=85048414110&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85048414110&partnerID=8YFLogxK

U2 - 10.1039/c8cy00112j

DO - 10.1039/c8cy00112j

M3 - Article

AN - SCOPUS:85048414110

VL - 8

SP - 2784

EP - 2788

JO - Catalysis Science and Technology

JF - Catalysis Science and Technology

SN - 2044-4753

IS - 11

ER -