TY - JOUR
T1 - Ullmann coupling reaction of 1,3-bistriflate esters of calix[4]arenes
T2 - facile syntheses of monoaminocalix[4]arenes and 4,4′:6,6′-diepithiobis(phenoxathiine)
AU - Tanaka, Shinya
AU - Serizawa, Ryuichi
AU - Morohashi, Naoya
AU - Hattori, Tetsutaro
N1 - Funding Information:
This study was supported in part by Grants-in-Aid for Scientific Research (No. 18037004 and No. 19550100) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
PY - 2007/10/22
Y1 - 2007/10/22
N2 - Treatment of 1,3-bistriflate esters of thiacalix- (6a) and calix[4]arenes 6b with benzylamine in the presence of CuI and K3PO4 results in the displacement of a TfO moiety with a benzylamino group, which provides an easy access to monoaminothiacalix[4]arene 4a and its methylene-bridged counterpart 4b. On the other hand, the reaction of 6a in the absence of benzylamine leads to intramolecular dietherification, giving 4,4′:6,6′-diepithiobis(phenoxathiine) 7a.
AB - Treatment of 1,3-bistriflate esters of thiacalix- (6a) and calix[4]arenes 6b with benzylamine in the presence of CuI and K3PO4 results in the displacement of a TfO moiety with a benzylamino group, which provides an easy access to monoaminothiacalix[4]arene 4a and its methylene-bridged counterpart 4b. On the other hand, the reaction of 6a in the absence of benzylamine leads to intramolecular dietherification, giving 4,4′:6,6′-diepithiobis(phenoxathiine) 7a.
KW - Aminocalixarenes
KW - Intramolecularly-bridged calixarene
KW - Ullmann coupling reaction
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U2 - 10.1016/j.tetlet.2007.08.095
DO - 10.1016/j.tetlet.2007.08.095
M3 - Article
AN - SCOPUS:34548847154
SN - 0040-4039
VL - 48
SP - 7660
EP - 7664
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 43
ER -