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The Synthesis of Group 10 and 11 Metal Complexes of 3,6,9‐Trithia‐1‐(2,6)‐pyridinacyclodecaphane and Their Use in A 3 ‐Coupling Reactions
Author(s) -
Rasheed Omer K.,
Bawn Carlo,
Davies David,
Raftery James,
VitoricaYrzebal Iñigo,
Pritchard Robin,
Zhou Huimin,
Quayle Peter
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701033
Subject(s) - chemistry , catalysis , toluene , metal , coupling reaction , group (periodic table) , crystal structure , medicinal chemistry , photochemistry , organic chemistry
The reaction between 3,6,9‐trithia‐1(2,6)‐pyridinacyclodecaphane and representative group 10 and 11 metal salts [Cu(NO 3 ) 2 , NiCl 2 or Ag(CF 3 CO 2 )] afforded 1:1 complexes, which in the case of Cu II and Ag I were characterised by single‐crystal X‐ray crystallography. The catalytic activity of these complexes in A 3 ‐coupling reactions between aldehydes, terminal alkynes and amines was assessed in both protic (water) and aprotic (toluene) media. These A 3 ‐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.