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Diamination of Conjugated Dienes and Trienes Catalyzed by N-Heterocyclic Carbene−Pd(0) Complexes

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Liang Xu, Haifeng Du, and Yian Shi*

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 yian@lamar.colostate.edu

J. Org. Chem., 2007, 72 (18), pp 7038–7041

DOI: 10.1021/jo0709394

Publication Date (Web): August 4, 2007

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Abstract

This paper describes a diamination process using di-t-butyldiaziridinone as nitrogen source and N-heterocyclic carbene−Pd(0) complex as catalyst. A wide variety of conjugated dienes and trienes can be effectively diaminated in good yields with high regio- and stereoselectivities.

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Citing Articles

View all 37 citing articles

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species
Baoguo Zhao, Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Richard G. Cornwall, and Yian Shi
Journal of the American Chemical Society2011 133 (51), 20890-20900
- Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species
  Baoguo Zhao, Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Richard G. Cornwall, and Yian Shi
  Journal of the American Chemical Society2011 133 (51), 20890-20900
  Conjugated dienes can be diaminated at the internal and/or terminal double bonds using Cu(I) as catalyst and N,N-di-t-butyldiaziridinone (1) as nitrogen source. The regioselectivity is highly dependent upon the choice of Cu(I) catalyst and the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications
Richard I. McDonald, Guosheng Liu, and Shannon S. Stahl
Chemical Reviews2011 111 (4), 2981-3019
- Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications
  Richard I. McDonald, Guosheng Liu, and Shannon S. Stahl
  Chemical Reviews2011 111 (4), 2981-3019
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination
Baoguo Zhao, Haifeng Du and Yian Shi
The Journal of Organic Chemistry2009 74 (21), 8392-8395
- Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination
  Baoguo Zhao, Haifeng Du and Yian Shi
  The Journal of Organic Chemistry2009 74 (21), 8392-8395
  Various achiral and chiral Cu(I) salts have been prepared from mesitylcopper(I) and investigated for the diamination of conjugated olefins with 1,3-di-tert-butyldiaziridinone as nitrogen source. It has been found that copper(I) phosphate has high ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
N-Heterocyclic Carbenes in Late Transition Metal Catalysis
Silvia Díez-González, Nicolas Marion and Steven P. Nolan
Chemical Reviews2009 109 (8), 3612-3676
- N-Heterocyclic Carbenes in Late Transition Metal Catalysis
  Silvia Díez-González, Nicolas Marion and Steven P. Nolan
  Chemical Reviews2009 109 (8), 3612-3676
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Theoretical Investigations on Mechanisms of Pd(OAc)₂-Catalyzed Intramolecular Diaminations in the Presence of Bases and Oxidants
Haizhu Yu, Yao Fu, Qingxiang Guo and Zhenyang Lin
Organometallics2009 28 (15), 4507-4512
- Theoretical Investigations on Mechanisms of Pd(OAc)₂-Catalyzed Intramolecular Diaminations in the Presence of Bases and Oxidants
  Haizhu Yu, Yao Fu, Qingxiang Guo and Zhenyang Lin
  Organometallics2009 28 (15), 4507-4512
  DFT calculations have been carried out to study the mechanisms of Pd(OAc)2-catalyzed intramolecular diamination reactions in the presence of bases and oxidants. On the basis of the calculation results, a mechanism involving an anti-aminopalladation/syn-C...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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History

Published In Issue August 31, 2007
Received May 5, 2007

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Note

Diamination of Conjugated Dienes and Trienes Catalyzed by N-Heterocyclic Carbene−Pd(0) Complexes

Abstract

Citing Articles

Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species

Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species

Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications

Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications

Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination

Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination

N-Heterocyclic Carbenes in Late Transition Metal Catalysis

N-Heterocyclic Carbenes in Late Transition Metal Catalysis

Theoretical Investigations on Mechanisms of Pd(OAc)₂-Catalyzed Intramolecular Diaminations in the Presence of Bases and Oxidants