The synthesis of group 10 and 11 metal complexes of 3,6,9-trithia- 1-(2,6)-pyridinacyclodecaphane and their use in A3-coupling reactions

Peter Quayle; Carlo  Brawn; David Davies; James Raftery; Inigo Vitorica-Yrezabal; Robin Pritchard; Huimin  Zhou

doi:10.1002/ejoc.201701033

The synthesis of group 10 and 11 metal complexes of 3,6,9-trithia- 1-(2,6)-pyridinacyclodecaphane and their use in A3-coupling reactions

Peter Quayle, Carlo Brawn, David Davies, James Raftery, Inigo Vitorica-Yrezabal, Robin Pritchard, Huimin Zhou

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

210 Downloads (Pure)

Abstract

The reaction between 3,6,9-trithia-1(2,6)-pyridinacyclodecaphane and representative group 10 and 11 metal salts [Cu(NO3)2, NiCl2 or Ag(CF3CO2 )] afforded 1:1 complexes which in the case of Cu(II) and Ag(I) were characterized by single crystal X-ray crystallography. The catalytic activity of these complexes in A3-coupling reactions between aldehydes, terminal alkynes and amines was assessed in both protic (water) and aprotic (toluene) media. These A3-reactions prove to be more efficient, proceed with lower catalyst loadings and with faster reaction rates, when conducted in a focused microwave reactor as compared to the same reactions promoted by standard, thermal, modes of activation

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	35
Early online date	4 Aug 2017
DOIs	https://doi.org/10.1002/ejoc.201701033
Publication status	Published - 2017

Access to Document

10.1002/ejoc.201701033

Quayle_et_al-2017-European_Journal_of_Organic_ChemistryAccepted author manuscript, 1.84 MB

CCDC 1542953: Experimental Crystal Structure Determination
Rasheed, O. K. (Contributor), Bawn, C. (Contributor), Davies, D. (Contributor), Raftery, J. (Contributor), Vitorica-Yrzebal, I. (Contributor), Pritchard, R. (Contributor), Zhou, H. (Contributor) & Quayle, P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nskpp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nskpp&sid=DataCite
Dataset
CCDC 1542952: Experimental Crystal Structure Determination
Rasheed, O. K. (Contributor), Bawn, C. (Contributor), Davies, D. (Contributor), Raftery, J. (Contributor), Vitorica-Yrzebal, I. (Contributor), Pritchard, R. (Contributor), Zhou, H. (Contributor) & Quayle, P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nsknn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nsknn&sid=DataCite
Dataset
CCDC 1542954: Experimental Crystal Structure Determination
Rasheed, O. K. (Contributor), Bawn, C. (Contributor), Davies, D. (Contributor), Raftery, J. (Contributor), Vitorica-Yrzebal, I. (Contributor), Pritchard, R. (Contributor), Zhou, H. (Contributor) & Quayle, P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nskqq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nskqq&sid=DataCite
Dataset

Cite this

@article{39ff679143234bf49d06250d8c39bc30,

title = "The synthesis of group 10 and 11 metal complexes of 3,6,9-trithia- 1-(2,6)-pyridinacyclodecaphane and their use in A3-coupling reactions",

abstract = "The reaction between 3,6,9-trithia-1(2,6)-pyridinacyclodecaphane and representative group 10 and 11 metal salts [Cu(NO3)2, NiCl2 or Ag(CF3CO2 )] afforded 1:1 complexes which in the case of Cu(II) and Ag(I) were characterized by single crystal X-ray crystallography. The catalytic activity of these complexes in A3-coupling reactions between aldehydes, terminal alkynes and amines was assessed in both protic (water) and aprotic (toluene) media. These A3-reactions prove to be more efficient, proceed with lower catalyst loadings and with faster reaction rates, when conducted in a focused microwave reactor as compared to the same reactions promoted by standard, thermal, modes of activation",

author = "Peter Quayle and Carlo Brawn and David Davies and James Raftery and Inigo Vitorica-Yrezabal and Robin Pritchard and Huimin Zhou",

year = "2017",

doi = "10.1002/ejoc.201701033",

language = "English",

volume = "2017",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "John Wiley & Sons Ltd",

number = "35",

}

TY - JOUR

T1 - The synthesis of group 10 and 11 metal complexes of 3,6,9-trithia- 1-(2,6)-pyridinacyclodecaphane and their use in A3-coupling reactions

AU - Quayle, Peter

AU - Brawn, Carlo

AU - Davies, David

AU - Raftery, James

AU - Vitorica-Yrezabal, Inigo

AU - Pritchard, Robin

AU - Zhou, Huimin

PY - 2017

Y1 - 2017

N2 - The reaction between 3,6,9-trithia-1(2,6)-pyridinacyclodecaphane and representative group 10 and 11 metal salts [Cu(NO3)2, NiCl2 or Ag(CF3CO2 )] afforded 1:1 complexes which in the case of Cu(II) and Ag(I) were characterized by single crystal X-ray crystallography. The catalytic activity of these complexes in A3-coupling reactions between aldehydes, terminal alkynes and amines was assessed in both protic (water) and aprotic (toluene) media. These A3-reactions prove to be more efficient, proceed with lower catalyst loadings and with faster reaction rates, when conducted in a focused microwave reactor as compared to the same reactions promoted by standard, thermal, modes of activation

AB - The reaction between 3,6,9-trithia-1(2,6)-pyridinacyclodecaphane and representative group 10 and 11 metal salts [Cu(NO3)2, NiCl2 or Ag(CF3CO2 )] afforded 1:1 complexes which in the case of Cu(II) and Ag(I) were characterized by single crystal X-ray crystallography. The catalytic activity of these complexes in A3-coupling reactions between aldehydes, terminal alkynes and amines was assessed in both protic (water) and aprotic (toluene) media. These A3-reactions prove to be more efficient, proceed with lower catalyst loadings and with faster reaction rates, when conducted in a focused microwave reactor as compared to the same reactions promoted by standard, thermal, modes of activation

U2 - 10.1002/ejoc.201701033

DO - 10.1002/ejoc.201701033

M3 - Article

SN - 1099-0690

VL - 2017

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

The synthesis of group 10 and 11 metal complexes of 3,6,9-trithia- 1-(2,6)-pyridinacyclodecaphane and their use in A3-coupling reactions

Abstract

Access to Document

Fingerprint

Datasets

CCDC 1542953: Experimental Crystal Structure Determination

CCDC 1542952: Experimental Crystal Structure Determination

CCDC 1542954: Experimental Crystal Structure Determination

Cite this