SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 20, 2007, Pages 3206-3208

Versatile Suzuki-Miyaura coupling reaction using diphenylvinylphosphine ligands

(4) Suzuki, Ken a Fontaine, Arnaud a Hori, Yoji a Kobayashi, Tohru a

a TAKASAGO INTERNATIONAL CORPORATION (Japan)

Author keywords

Biaryls; Cross coupling; Halides; Ligands; Palladium

Indexed keywords

2,2 DIPHENYLVINYLPHOSPHINE DERIVATIVE; BIPHENYL DERIVATIVE; BORONIC ACID DERIVATIVE; HALIDE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; SUZUKI REACTION;

EID: 37749055147 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-992371 Document Type: Article

Times cited : (10)

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29
- 37749005865
- For the preparation of 1b and 1c, see ref. 9. Representative Procedure for the Preparation of 1a: A solution of 2-bromo-1,1-diphenylpropene9 (25.0 g, 91.5 mmol) and magnesium turnings (2.35 g, 96.1 mmol) in THF (100 mL) was stirred at r.t. under a nitrogen atmosphere. After addition of a piece of iodine, the solution was refluxed for 2 h. Then chlorodiisopropylphosphine (16.8 g, 109.8 mmol) was added dropwise at the same temperature and the mixed solution was refluxed for 18 h. After cooling to r.t, H2O was added to the solution and the organic phase was extracted with toluene. The extract was dried over anhyd MgSO 4 and concentrated under reduced pressure. The concentrate was purified by recrystallization from MeOH (100 mL) to give the title compound (18.8 g, 66, as a white solid. 1H NMR (300 MHz, CDCl3, δ, 1.07 (dd, J, 2.0, 7.1 Hz, 6 H, 1.12 (dd, J, 5.7, 6.3 Hz, 6 H, 1.80-2.04 m
- 27P: 311.1929; found: 311.1916.

30
- 37749033325
- Ligands 1a-c are solids stable enough to moisture and oxidation by molecular oxygen that they could be to be handled under air.
- Ligands 1a-c are solids stable enough to moisture and oxidation by molecular oxygen that they could be to be handled under air.

31
- 37749030317
- Typical Procedure for the Coupling Reaction: Aryl halide (1.0 equiv) and arylboronic acid (1.2 equiv) were added to a solution of KF (2.0 equiv, Pd(OAc)2 (1.0 mol, and ligand (2.0 mol, in toluene (0.5 M) at r.t. under a nitrogen atmosphere. The solution was stirred at 80°C for 1-3 h. After cooling to r.t, the solution was diluted with toluene, washed with H2O and brine, dried over anhyd MgSO4 and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography to give the coupling products. 4-Methoxybiphenyl (Table 1, entry 1, 1H NMR (200 MHz, CDCl3, δ, 3.85 (s, 3 H, 7.04-6.93 (m, 2 H, 7.60-7.23 (m, 7 H, 13C NMR 50 MHz, CDCl3, δ, 55.3, 114.2, 126.6, 126.7, 128.1, 128.7, 133.8, 140.8, 159.1
- 3): δ = 55.3, 114.2, 126.6, 126.7, 128.1, 128.7, 133.8, 140.8, 159.1.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.