Highly chemoselective reduction of imines using a AuNPore/PhMe2SiH/water system and its application to reductive amination

Balaram S. Takale; Shanmou Tao; Xiaoqiang Yu; Xiujuan Feng; Tienan Jin; Ming Bao; Yoshinori Yamamoto

doi:10.1016/j.tet.2014.11.023

Highly chemoselective reduction of imines using a AuNPore/PhMe₂SiH/water system and its application to reductive amination

Balaram S. Takale, Shanmou Tao, Xiaoqiang Yu, Xiujuan Feng, Tienan Jin, Ming Bao, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

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

23 Citations (Scopus)

Abstract

Abstract An unusually strong affinity of unsupported nanoporous gold (AuNPore) towards aldimines and ketimines has been demonstrated. By using PhMe₂SiH and water as a hydrogen source and AuNPore as a catalyst, ketimines and aldimines can be reduced to the corresponding amines in high chemical yields under mild conditions. This system was also applied to the reductive amination of aldehydes and ketones.

Original language	English
Article number	26172
Pages (from-to)	7154-7158
Number of pages	5
Journal	Tetrahedron
Volume	71
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2014.11.023
Publication status	Published - 2015 Aug 17

Keywords

Amine
Heterogeneous catalysis
Imine
Nanoporous gold
Reductive amination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2014.11.023

Cite this

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title = "Highly chemoselective reduction of imines using a AuNPore/PhMe2SiH/water system and its application to reductive amination",

abstract = "Abstract An unusually strong affinity of unsupported nanoporous gold (AuNPore) towards aldimines and ketimines has been demonstrated. By using PhMe2SiH and water as a hydrogen source and AuNPore as a catalyst, ketimines and aldimines can be reduced to the corresponding amines in high chemical yields under mild conditions. This system was also applied to the reductive amination of aldehydes and ketones.",

keywords = "Amine, Heterogeneous catalysis, Imine, Nanoporous gold, Reductive amination",

author = "Takale, {Balaram S.} and Shanmou Tao and Xiaoqiang Yu and Xiujuan Feng and Tienan Jin and Ming Bao and Yoshinori Yamamoto",

note = "Funding Information: We are grateful to the National Natural Science Foundation of China (NSFC-IUPAC program, No. 21361140375 ) for their financial support. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

year = "2015",

month = aug,

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doi = "10.1016/j.tet.2014.11.023",

language = "English",

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T1 - Highly chemoselective reduction of imines using a AuNPore/PhMe2SiH/water system and its application to reductive amination

AU - Takale, Balaram S.

AU - Tao, Shanmou

AU - Yu, Xiaoqiang

AU - Feng, Xiujuan

AU - Jin, Tienan

AU - Bao, Ming

AU - Yamamoto, Yoshinori

N1 - Funding Information: We are grateful to the National Natural Science Foundation of China (NSFC-IUPAC program, No. 21361140375 ) for their financial support. Publisher Copyright: © 2014 Elsevier Ltd.

PY - 2015/8/17

Y1 - 2015/8/17

N2 - Abstract An unusually strong affinity of unsupported nanoporous gold (AuNPore) towards aldimines and ketimines has been demonstrated. By using PhMe2SiH and water as a hydrogen source and AuNPore as a catalyst, ketimines and aldimines can be reduced to the corresponding amines in high chemical yields under mild conditions. This system was also applied to the reductive amination of aldehydes and ketones.

AB - Abstract An unusually strong affinity of unsupported nanoporous gold (AuNPore) towards aldimines and ketimines has been demonstrated. By using PhMe2SiH and water as a hydrogen source and AuNPore as a catalyst, ketimines and aldimines can be reduced to the corresponding amines in high chemical yields under mild conditions. This system was also applied to the reductive amination of aldehydes and ketones.

KW - Amine

KW - Heterogeneous catalysis

KW - Imine

KW - Nanoporous gold

KW - Reductive amination

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