Non-deprotonative primary and secondary amination of (hetero)arylmetals

Zhe Zhou; Zhiwei Ma; Nicole Erin Behnke; Hongyin Gao; László Kürti

doi:10.1021/jacs.6b12712

Non-deprotonative primary and secondary amination of (hetero)arylmetals

Zhe Zhou, Zhiwei Ma, Nicole Erin Behnke, Hongyin Gao, László Kürti

Biochemistry

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

46 Scopus citations

Abstract

Herein we disclose a novel method for the facile transfer of primary (-NH₂) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.

Original language	English (US)
Pages (from-to)	115-118
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	1
DOIs	https://doi.org/10.1021/jacs.6b12712
State	Published - Jan 11 2017

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Non-deprotonative primary and secondary amination of (hetero)arylmetals",

abstract = "Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.",

author = "Zhe Zhou and Zhiwei Ma and Behnke, {Nicole Erin} and Hongyin Gao and L{\'a}szl{\'o} K{\"u}rti",

note = "Funding Information: L.K. gratefully acknowledges the generous financial support of Rice University, National Institutes of Health (R01 GM-114609-01), National Science Foundation (CAREER:SusChEM CHE' 1455335), the Robert A. Welch Foundation (Grant C-l764). ACS-PRF (Grant 51707-DNIl), Amgen (2014 Young Investigators' Award for LK) and Biotage (2015 Young Principe Investigator Award). We thank Professor Daniel H. Ess (BYU) for helpful discussions. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/jacs.6b12712",

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T1 - Non-deprotonative primary and secondary amination of (hetero)arylmetals

AU - Zhou, Zhe

AU - Ma, Zhiwei

AU - Behnke, Nicole Erin

AU - Gao, Hongyin

AU - Kürti, László

N1 - Funding Information: L.K. gratefully acknowledges the generous financial support of Rice University, National Institutes of Health (R01 GM-114609-01), National Science Foundation (CAREER:SusChEM CHE' 1455335), the Robert A. Welch Foundation (Grant C-l764). ACS-PRF (Grant 51707-DNIl), Amgen (2014 Young Investigators' Award for LK) and Biotage (2015 Young Principe Investigator Award). We thank Professor Daniel H. Ess (BYU) for helpful discussions. Publisher Copyright: © 2016 American Chemical Society.

PY - 2017/1/11

Y1 - 2017/1/11

N2 - Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.

AB - Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.

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Non-deprotonative primary and secondary amination of (hetero)arylmetals

Abstract

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