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Volumn 26, Issue 7, 2007, Pages 1578-1580

Pendant alkenes promote cobalt-cobalt bond cleavage in (alkyne)(binap) tetracarbonyldicobalt(0) complexes

(6) Gibson, Susan E a Kaufmann, Karina A C a Haycock, Peter R a White, Andrew J P a Hardick, David J b Tozer, Matthew J b

a IMPERIAL COLLEGE LONDON (United Kingdom)

b MEDIVIR AB (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPOUNDS; COMPLEXATION; COVALENT BONDS; HYDRIDES; REACTION KINETICS;

ALKYNES; BOND CLEAVAGE;

OLEFINS;

EID: 34047273591 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om070022v Document Type: Article

Times cited : (21)

References (28)

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20
- 34047267086
- Octacarbonyldicobalt(0, 75 mg, 0.220 mmol) and (±)-2,2′- bis(diphenylphosphino)-1,1′-binaphthalene (140 mg, 0.225 mmol) were dissolved in THF (15 mL) and stirred at room temperature for 30 min. The mixture was heated to 40°C for 30 min. N-(Prop-2-enyl)-N-(prop-2-ynyl)-p- toluenesulfonamide9 (56 mg, 0.226 mmol) was added, and the reaction mixture was stirred at 40°C for 2 h. The mixture was cooled to room temperature and was then absorbed onto neutral alumina (grade II, The brown solid was loaded onto a chromatography column (silica) and eluted under nitrogen, first with hexane/ethyl acetate (19:1) to remove unreacted octacarbonyldicobalt(0) and then with hexane/ethyl acetate (7:3) to collect 3 as a brown solid (109 mg, 45, IR (CHCl3, cm-1, v CO 2043 (s, 1980 (s, 1939 (s, 31P NMR (160 MHz, DME, δ 59.4, 53.2, 44.0, 40.0 (CoPPh2-Ar, 14.6 (binap; <5, MS (FAB, m/z, ) 1017 M
- +, 65].

21
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23
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- Complex 3 (35 mg) was dissolved in CO-saturated DME (0.8 mL) and syringed via a filter needle into a WILMAD screw-cap (with a PTFE/ silicone septum) NMR tube filled with carbon monoxide; 31P NMR spectra were recorded between 30 and 75°C (see Figure 4, The NMR tube was then cooled to 30°C, and the 31P NMR spectrum was recorded at this temperature. 31P NMR (160 MHz, DME, δ 53.4, 43.2 (CoPPh2Ar, 14.2 (binap; <5, When the NMR tube was stored in the freezer, small brown crystals appeared in the NMR tube and these were identified as hydride 7 by X-ray crystallography.13 The early stages of the experiment were subsequently repeated in d8-THF. When the temperature was lowered to 30°C, the 31P and 1H NMR spectra were recorded. 31P NMR (160 MHz, d8-THF, δ 52.9, 42.6. 1H NMR (400 MHz, d8-THF, δ-11.6 broad, Co-H
- 8-THF): δ-11.6 (broad, Co-H).

24
- 34047246769
- Crystal data for 7: C46H33CoO2P 2, Mr, 738.59, monoclinic. P21/n (No. 14, a, 15.0501(7) Å, b, 14.7142(7) Å, c, 17.0825(8) Å, β= 110.517(4)°, V, 3543.0(3) Å3, Z, 4, Dc, 1.385 g cm-3, μMo Ka, 0.615 mm-1, T, 173 K, brown needles, Oxford Diffraction Xcalibur 3 diffractometer, 12 274 independent measured reflections, F2 refinement, R1, 0.094, wR2, 0.114, 5717 independent observed reflections, Fo| > 4σ, Fo, 2θmax, 65°, 464 parameters. CCDC 619746
- max = 65°), 464 parameters. CCDC 619746.

25
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27
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- Comely, A.C.¹ Gibson, S.E.² Hales, N.J.³ Johnstone, C.⁴ Stevenazzi, A.⁵

28
- 34047269705
- 31P NMR spectroscopy gave resonances at δ 54 and 43 which simplified after 2 h to a single resonance at δ 43.
- 31P NMR spectroscopy gave resonances at δ 54 and 43 which simplified after 2 h to a single resonance at δ 43.

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