Nico Weding et al.
FULL PAPERS
lution in ether), 2 or 3 (0.1 mol%) in toluene (20 mL). The
reaction mixture was transferred into an autoclave, which
was then heated to 808C under introduction of syngas. After
2 h the temperature of the reaction mixture was raised to
1208C in the case of 1 and 3 and to 1008C for 2. Following
22 h reaction time, the autoclave was allowed to cool down
to room temperature, and the pressure was released. The re-
action mixture was analyzed immediately by gas chromatog-
raphy.
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General procedure for the catalytic hydrogenation of 1-
octene (17): The olefin (17, 1.0 mmol) was added under
argon to a solution of the metal precursor (2.0 mol%) in tol-
uene (20 mL). The reaction mixture was transferred into an
autoclave, which was then heated to 608C. Hydrogen was
then introduced and heating continued for 2 h, then the re-
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temperature, and the pressure was released. The reaction
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General procedure for the catalytic hydroboration of sty-
rene (22) with catecholborane: To a solution of 22 (0.1 g,
1.0 mmol) and HBcat (1.0 mmol, 1M in THF) in THF
(3 mL) a solution of the catalyst (5 mol% in the case of 1 in
Et2O and for 2 and 3 in 0.5 mL THF), was added dropwise
and the mixture stirred for 2 h at room temperature. After
quenching with EtOH (2 mL) the solution was mixed with
NaOH (2M, 4 mL) and H2O2 (4 mL, 30% v/v in water). The
slurry was stirred for 3 h, before the reation mixture was ex-
tracted with Et2O several times. The combined organic
phases were washed with brine and NaOH (2M) and dried
with MgSO4. Traces of product 23 were identified by GC
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1
and H NMR.[32]
Acknowledgements
This work was supported by the LIKAT. We thank Prof.
Uwe Rosenthal for his support and helpful discussions and
comments. Fabian Fischer is thanked for excellent and skilful
support of the experimental work.
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ꢃ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2011, 353, 3423 – 3433