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Volumn 15, Issue 46, 2009, Pages 12636-12643

Dendron-functionalized core - shell superparamagnetic nanoparticles: magnetically recoverable and reusable catalysts for suzuki C - C Cross-Coupling reactions

Author keywords

Cross coupling; Dendrons; Heterogeneous catalysis; Nanoparticles; Supported catalysts

Indexed keywords

CATALYSIS; CATALYST SUPPORTS; DENDRIMERS; GRAFTING (CHEMICAL); NANOMAGNETICS; NANOPARTICLES; PALLADIUM COMPOUNDS; SHELLS (STRUCTURES); SUPERPARAMAGNETISM;

EID: 71649103615     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901866     Document Type: Article
Times cited : (74)

References (128)
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    • US 4017694
    • b) J. A. King, US 4017694, 1977;
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    • King, J.A.1
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    • [Chem. Abstr. 1992,116, 129870];
    • (1992) Chem. Abstr. , vol.116 , pp. 129870
  • 107
    • 71649098124 scopus 로고    scopus 로고
    • See general procedure for catalytic reactions and recovery of catalysts with 5 mg of grafted MNPs, iodobenzene, and phenylboronic acid in THF/Tx (2/1) at RT. Conversions were determined by GC analysis
    • See general procedure for catalytic reactions and recovery of catalysts with 5 mg of grafted MNPs, iodobenzene, and phenylboronic acid in THF/Tx (2/1) at RT. Conversions were determined by GC analysis.
  • 108
    • 71649106391 scopus 로고    scopus 로고
    • PF127: Pluronic F127 aqueous solution (0.3 wt%) obtained from Pluronic F127 (Aldrich)
    • PF127: Pluronic F127 aqueous solution (0.3 wt%) obtained from Pluronic F127 (Aldrich).
  • 109
    • 71649085443 scopus 로고    scopus 로고
    • 2-(N-Morpholino)ethanesulfonic acid (50 mm) in an aqueous solution of PF127 (see ref. [25])
    • 2-(N-Morpholino)ethanesulfonic acid (50 mm) in an aqueous solution of PF127 (see ref. [25]).
  • 110
    • 71649086350 scopus 로고    scopus 로고
    • HLB: hydrophilic/lipophilic balance. HLB(Pluronic F127)=22, HLB(tritonX405) = 17.9
    • HLB: hydrophilic/lipophilic balance. HLB(Pluronic F127)=22, HLB(tritonX405) = 17.9.
  • 111
    • 71649092391 scopus 로고    scopus 로고
    • Tx: triton X405 aqueous solution (0.21%) obtained from triton X405 (70%) purchased from Aldrich
    • Tx: triton X405 aqueous solution (0.21%) obtained from triton X405 (70%) purchased from Aldrich.
  • 112
    • 71649097618 scopus 로고    scopus 로고
    • Ten times more dilute medium. Total reaction volume was 10 mL
    • Ten times more dilute medium. Total reaction volume was 10 mL.
  • 113
    • 71649095858 scopus 로고    scopus 로고
    • -1). Total reaction volume was 1 mL
    • -1). Total reaction volume was 1 mL.
  • 114
    • 71649086732 scopus 로고    scopus 로고
    • See general procedure for catalytic reactions and recovery of catalysts with 2.5 mg of grafted MNPs, iodobenzene, and phenylboronic acid at RT in THF/Tx (2/1). After 1.5 h, we obtained 100% conversion with CHMC or EDC in the first cycle and 100% conversion (with CHMC, in 14 h) and 98% conversion (with EDC, in 16 h) in the second cycle
    • See general procedure for catalytic reactions and recovery of catalysts with 2.5 mg of grafted MNPs, iodobenzene, and phenylboronic acid at RT in THF/Tx (2/1). After 1.5 h, we obtained 100% conversion with CHMC or EDC in the first cycle and 100% conversion (with CHMC, in 14 h) and 98% conversion (with EDC, in 16 h) in the second cycle.
  • 115
    • 71649101928 scopus 로고    scopus 로고
    • -1)
    • -1).
  • 116
    • 71649088425 scopus 로고    scopus 로고
    • Accessible free carboxyl groups amount to 300-355 μmol per gram of particles, determined by conductimetric measurements
    • Accessible free carboxyl groups amount to 300-355 μmol per gram of particles, determined by conductimetric measurements.
  • 117
    • 71649115018 scopus 로고    scopus 로고
    • Pd ICP analyses of grafted MNPs were 1.83 and 3.8%, respectively, for 2 and 10 equivalents of 9 in the grafting reaction
    • Pd ICP analyses of grafted MNPs were 1.83 and 3.8%, respectively, for 2 and 10 equivalents of 9 in the grafting reaction.
  • 123
    • 71649110705 scopus 로고    scopus 로고
    • note
    • 3/polymer 500 nm superparamagnetic nanoparticles (Carboxyl-Adembeads 500 nm, Ademtech, France, 250 μmol COOH per gram of particles).
  • 124
    • 71649109193 scopus 로고    scopus 로고
    • note
    • Catalytic tests were performed with 0.125 mg of grafted MNP materials according to the general procedure (see Experimental Section).
  • 125
    • 71649086895 scopus 로고    scopus 로고
    • note
    • For coupling of bromobenzene and phenylboronic acid with NaOH in Tx/THF (9/1), at 65°C for 4 h, with 2.5 mg of catalyst (2.4 mol% Pd) we obtained 99 and 97% yield for 300 and 200 nm MNPs, respectively.
  • 126
    • 71649113965 scopus 로고    scopus 로고
    • note
    • See general procedure: Grafted MNPs with 2equiv of dendron 9 (5mg, 1.96 mol% Pd), NaOH (168 umol), phenylboronic acid (84.37 umol), and iodobenzene (56.25 μmol) were mixed in 1 mL of Tx/THF (9/1). The mixture was stirred at 65°C for 1 h. Then grafted MNPs were separated from the mixture by an external magnet and were washed with Tx/THF (9/1, (2×500 μL). Particles were washed twice with Tx/THF (9/1) between each run.
  • 127
    • 71649113801 scopus 로고    scopus 로고
    • note
    • Suspension of Carboxyl-Adembeads 300 nm nanoparticles 1 wt % MeOH/Tx(1:2).
  • 128
    • 71649114146 scopus 로고    scopus 로고
    • note
    • -1 in MeOH/Tx (1:2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.