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Volumn 120, Issue 38, 1998, Pages 9971-9972

Reactive dyes as a method for rapid screening of homogeneous catalysts [16]

Author keywords

[No Author keywords available]

Indexed keywords

DYE; PHOSPHINE DERIVATIVE;

BLEACHING; CATALYST; COLOR; DRUG SCREENING; ELECTRON TRANSPORT; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032581922 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja9818607 Document Type: Letter

Times cited : (90)

References (25)

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- The reaction mixture was cooled to room temperature and the MgSO4 filtered off. The nitrate, concentrated under reduced pressure, gave a dark red solid, which was purified by chromatography on alumina with 10/90 (v/v) ethyl acetate/hexane. The dye was obtained as a red solid (1.9 g, 94% yield). H NMR (CDCl3 25 °C) 8.66 (d, J = 7.5 Hz. 2H), 8.56 (s, 1H), 7.63 (d, J = 7.5 Hz, 2H), 4.62 (t, J= 2.1 Hz. 2H), 4.36 (t, J = 2.1 Hz, 2H), 4.21 (s, 5H). Anal. Calcd for C16H14FeN2: C. 66.20; H. 4.86; N, 9.65, Found: C, 66.62; H, 4.88; N, 9.38. The pro-dyes 1 and 2 (3.46 mmol) were treated with 4-(rm-butyl)benzyl bromide (0.96 mL, 5.2 mmol) in DMF (50 mL) al 80 °C for 15 min. The cooled solution was poured into 1:1 (v/v) Et2O/hexanes (100 mL) to precipitate a dark-colored solid, which was filtered, washed with Et2O (3 x 30 mL), and dissolved in acetone (50 mL). Addition oi NaBPlu (1.2 g, 3.5 mmol), stirring for 12 h, and removal of the acetone in vacuo gave a solid which was extracted with CH2Cl2: (2 x 20 mL). Evaporation of the combined extracts and recrysiallization from 5:1 (v/ v) MeOH/THF gave crystals of the products 3 (78Vc) and 4 (86%), For an example, in DMSO, λ, (ϵ) 3 is 554 nm (62 000). This means that control wells need to be run in the same solvent during any catalyst assays
- max (ϵ) 3 is 554 nm (62 000). This means that control wells need to be run in the same solvent during any catalyst assays.
- 4 (0.5 G) for 2 H

16
- 85027993603
- 1H NMR (CDCl3,. 25 °C) of 4: 8.42 (s, 1H), 7.41 (m, 13H). 6.87 (m, 9H), 6.84 (m, 7H), 4.65 (1, J = 2.1 Hz, 2H), 4.57 (t, J = 1.8 Hz, 2H), 4.43 (s, 2H), 4.18 (s, 5H), 1.29 (s, 9H). Anal. Calcd for C51H49BFeN2:C, 81.0; H, 6.53; N, 3.70. Found: C, 80.68; H, 6.39; N, 3.70
- 2:C, 81.0; H, 6.53; N, 3.70. Found: C, 80.68; H, 6.39; N, 3.70.

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21
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- 2; was therefore used subsequently. (f) More of the less intensely colored imine dye was required per well than of the more intense alkene.
- 2; was Therefore Used Subsequently. (F) More of the less Intensely Colored Imine Dye was Required per Well than of the More Intense Alkene

22
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- Digital images for a sample screen, S0002-7863(98)01860-5 CCC: $15.00 © 1998 American Chemical Society
- Digital images for a sample screen are available on the Web at http://ursula.chem.yale.edu/~crabtree/ under “Research”. S0002-7863(98)01860-5 CCC: $15.00 © 1998 American Chemical Society

23
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- A glovebag, used in initial runs, was satisfactory for the more air-stable catalysts.
- A Glovebag, Used in Initial Runs, was Satisfactory for the More Air-Stable Catalysts

25
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- in preparation
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- Cooper, A.¹ Loch, J.² Crabtree, R.H.³

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