Biaryl formation via Suzuki and Stille coupling reactions using palladium nanoparticle/polymeric N-heterocyclic carbene grafted silica as recyclable and efficient catalyst

被引：11

作者：

Ghasemi, Soheila ^{[1
]}

Farjadian, Fatemeh ^{[1
,2
]}

Tamami, Bahman ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Coll Sci, POB 7194684795, Shiraz, Iran

[2] Shiraz Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, POB 71345-1583, Shiraz, Iran

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2016年 / 30卷 / 10期

关键词：

N-heterocyclic carbenes; palladium nanoparticles; polymer grafted silica; Suzuki reaction; Stille reaction; HETEROGENEOUS CATALYST; COMPLEXES; REAGENTS; HECK; SONOGASHIRA;

D O I：

10.1002/aoc.3508

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Palladium nanoparticles supported on polymeric N-heterocyclic carbene grafted silica as an efficient organic-inorganic hybrid catalyst is introduced. Pd-0 nanoparticle formation, which is stabilized by the polymeric N-heterocyclic carbene ligands and ionic liquid units, was confirmed using X-ray photoelectron spectroscopy. Scanning electron microscopy images showed microparticles of modified silica while transmission electron microscopy images displayed a fine distribution of Pd nanoparticles. The modified structure was applied successfully in biaryl formation via Suzuki and Stille coupling reactions. Various biaryls were generated through the reaction of phenylboronic acid or tetraphenyltin with a variety of haloarenes via cross-coupling reactions. This catalyst showed promising activity after being recycled several times. Copyright (C) 2016 John Wiley & Sons, Ltd.

引用

页码：818 / 822

页数：5

共 36 条

[1] Catalytic activities in the direct C5 arylation of novel palladium N-heterocyclic carbene complexes containing benzimidazol-2-ylidene nucleus [J].

Akkoc, Senem ;

Gok, Yetkin ;

Akkurt, Mehmet ;

Tahir, Muhammad Nawaz .

INORGANICA CHIMICA ACTA, 2014, 413 :221-230

[2] Synthetic Routes to N-Heterocyclic Carbene Precursors [J].

Benhamou, Laure ;

Chardon, Edith ;

Lavigne, Guy ;

Bellemin-Laponnaz, Stephane ;

Cesar, Vincent .

CHEMICAL REVIEWS, 2011, 111 (04) :2705-2733

[3] The Stille Reaction, 38 Years Later [J].

Cordovilla, Carlos ;

Bartolome, Camino ;

Martinez-Ilarduya, Jesus Ma ;

Espinet, Pablo .

ACS CATALYSIS, 2015, 5 (05) :3040-3053

[4]

Cragg P., 2010, CHEM LISTY, V104, P1064

[5] Stille coupling reactions catalysed by a polymer supported palladium complex [J].

Dell'Anna, MM ;

Lofù, A ;

Mastrorilli, P ;

Mucciante, V ;

Nobile, CF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (1-2) :131-137

[6] Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids [J].

Deshmukh, RR ;

Rajagopal, R ;

Srinivasan, KV .

CHEMICAL COMMUNICATIONS, 2001, (17) :1544-1545

[7] Phosphinite-functionalized silica and hexagonal mesoporous silica containing palladium nanoparticles in Heck coupling reaction: synthesis, characterization, and catalytic activity [J].

Farjadian, Fatemeh ;

Hosseini, Majid ;

Ghasemi, Soheila ;

Tamami, Bahman .

RSC ADVANCES, 2015, 5 (97) :79976-79987

[8] Poly(vinylpyridine)-Grafted Silica Containing Palladium or Nickel Nanoparticles as Heterogeneous Catalysts for the Sonogashira Coupling Reaction [J].

Farjadian, Fatemeh ;

Tamami, Bahman .

CHEMPLUSCHEM, 2014, 79 (12) :1767-1773

[9] Preparation, characterization and first application of silica supported palladium-N-heterocyclic carbene as a heterogeneous catalyst for C-C coupling reactions [J].

Ghiaci, Mehran ;

Zarghani, Monireh ;

Khojastehnezhad, Amir ;

Moeinpour, Farid .

RSC ADVANCES, 2014, 4 (30) :15496-15501

[10] One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes [J].

Gingras, Marc .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (03) :968-1006

← 1 2 3 4 →