Amphiphilic PdII‐NHC Complexes on 1,3‐Alternate p‐tert‐Butylthiacalixarene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

Herein we report the first example of amphiphilic PdII–NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII–NHC complexes in Suzuki–Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar...

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Published in:European journal of organic chemistry 2020-04, Vol.2020 (15), p.2180-2189
Main Authors: Burilov, Vladimir A, Mr Bulat Kh Gafiatullin, Mironova, Diana A, Sultanova, Elza D, Evtugyn, Vladimir G, Osin, Yuri N, Islamov, Daut R, Usachev, Konstantin S, Solovieva, Svetlana E, Antipin, Igor S
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Language:English
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Summary:Herein we report the first example of amphiphilic PdII–NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII–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. PdII–NHC complexes demonstrated a high activity in model hydrogenation reaction of p‐nitrophenol using sodium borohydride. The most lipophilic PdII–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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000059