Synlett 2005(1): 179-181  
DOI: 10.1055/s-2004-836058
LETTER
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Addition Reaction of Alcohols across Olefins

Yohei Oe, Tetsuo Ohta*, Yoshihiko Ito
Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto, 610-6394, Japan
Fax: +81(774)656789; e-Mail: tota@mail.doshisha.ac.jp;
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Publikationsverlauf

Received 14 September 2004
Publikationsdatum:
02. Dezember 2004 (online)

Abstract

2-Phenylethanol was added to olefins catalyzed by ruthenium catalytic system Cp*RuCl2(PPh3)/2AgOTf in toluene. This ­reaction proceeded without β-hydride elimination, giving saturated ethers in good yields.

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Typical Procedure of Ruthenium-Catalyzed Hydroalkoxylation Reaction of 2-Phenylethanol(1) with Styrene ( 2a) Described in Table 2, Entry 1.
Cp*RuCl2 (Ph3P) (11 mg, 0.02 mmol) was dissolved in toluene (2 mL) and the solution was heated to 85 °C. After 15 min, AgOTf (11.5 mg, 0.045 mmol) was added and stirred at 85 °C for 3 h. The reaction mixture was cooled to r.t. 2-Phenylethanol (1, 122 mg, 1.0 mmol) and styrene (2a, 260 mg, 2.5 mmol) were added. The reaction mixture was heated to 70 °C and stirred for 48 h. The crude product was purified by silica gel chromatography (hexane-EtOAc = 10:1), yielding product 3a (187 mg, 83%).