Amphiphilic PdII-NHC Complexes on 1,3-Alternate p-tert-Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions

被引：12

作者：

Burilov, Vladimir A. ^{[1
]}

Gafiatullin, Mr. Bulat Kh. ^{[1
]}

Mironova, Diana A. ^{[1
]}

Sultanova, Elza D. ^{[1
]}

Evtugyn, Vladimir G. ^{[1
]}

Osin, Yuri N. ^{[1
]}

Islamov, Daut R. ^{[2
]}

Usachev, Konstantin S. ^{[1
]}

Solovieva, Svetlana E. ^{[2
]}

Antipin, Igor S. ^{[1
]}

机构：

[1] Kazan Fed Univ, 18 Kremlevskaya St, Kazan 420008, Russia

[2] AE Arbuzov Inst Organ & Phys Chem, 8 Arbuzov Str, Kazan 420088, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 15期

基金：

俄罗斯科学基金会;

关键词：

NHC complex; Thiacalix[4]arene; Suzuki coupling; Micellar catalysis; Catalytic hydrogenation; N-HETEROCYCLIC CARBENE; SUZUKI-MIYAURA; ORGANIC-REACTIONS; NANOPARTICLES; DERIVATIVES; REACTIVITY; CHEMISTRY; AMINES;

D O I：

10.1002/ejoc.202000059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2180 / 2189

页数：10

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