TY - JOUR
T1 - Synthesis of propargylic ethers by gold-mediated reaction of terminal alkynes with acetals
AU - Furuta, Miyu
AU - Sugiyama, Kyoko
AU - Yamaguchi, Minami
AU - Ueda, Hirofumi
AU - Tokuyama, Hidetoshi
N1 - Funding Information:
Acknowledgments This work was supported by the Drug Discovery and Life Science Research (BINDS) from AMED (Grant Number JP18am0101100) and JSPS KAKENHI Grant Numbers JP18H04379, JP18H04231, JP18H04642, 18H02549, 17K08204 and 18H06100.
Publisher Copyright:
© 2019 The Pharmaceutical Society of Japan.
PY - 2019
Y1 - 2019
N2 - A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.
AB - A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.
KW - Acetal
KW - Gold catalysis
KW - Propargylic ether
KW - Terminal alkyne
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U2 - 10.1248/cpb.c19-00322
DO - 10.1248/cpb.c19-00322
M3 - Article
C2 - 31366835
AN - SCOPUS:85070562749
VL - 67
SP - 872
EP - 876
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 8
ER -