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Amphiphilic Pd II ‐NHC Complexes on 1,3‐Alternate p‐tert ‐Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions
Author(s) -
Burilov Vladimir A.,
Gafiatullin Mr. Bulat Kh.,
Mironova Diana A.,
Sultanova Elza D.,
Evtugyn Vladimir G.,
Osin Yuri N.,
Islamov Daut R.,
Usachev Konstantin S.,
Solovieva Svetlana E.,
Antipin Igor S.
Publication year - 2020
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.202000059
Subject(s) - phenylboronic acid , chemistry , catalysis , sodium borohydride , amphiphile , selectivity , medicinal chemistry , coupling reaction , suzuki reaction , polymer chemistry , palladium , combinatorial chemistry , organic chemistry , copolymer , polymer
Herein we report the first example of amphiphilic Pd II –NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized Pd II –NHC complexes in Suzuki–Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki–Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2‐fold increase of conversion of 4‐bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. Pd II –NHC complexes demonstrated a high activity in model hydrogenation reaction of p ‐nitrophenol using sodium borohydride. The most lipophilic Pd II –NHC complex was found to be most active, which can be attributed with additional p ‐nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle.