Aerobic oxidation of primary alcohols in the presence of activated secondary alcohols

Tetrahedron Letters

Volumn 46, Issue 5, 2005, Pages 783-786

  Egami, Hiromichi ^a   Shimizu, Hideki ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Aerobic oxidation; Aldehyde; Oxygen; Photo irradation; Primary alcohol; Ru(salen) complex

Indexed keywords

1 PHENYLETHANOL; ALCOHOL DERIVATIVE; DECANOL; METHYL GROUP; NITROSO DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CATALYST; COMPLEX FORMATION; LIGHT IRRADIANCE; LOW TEMPERATURE; NITROSYLATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 11844252598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.010     Document Type: Article

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40. In the course of our study on asymmetric desymmetrization of meso-diols using (ON)Ru(salen) complexes as catalysts, we found that the nature of the apical ligands of the complexes affects the selectivity of the reaction (Ref. 8b)
41. 3,5-Di(1-ethyl-1methylpropyl)-2-hydroxybenzaldehyde was prepared from phenol in five steps: (i) treatment of phenol with 3-methyl-2-pentene (1 equiv) in the presence of HY zeolite (30 wt%) at 80°C (95%), (ii) treatment of the resulting 5-(1-ethyl-1methylpropyl)phenol with 3-methyl-2-pentene (0.35 equiv) in the presence of HY zeolite (30 wt%) at 80°C (85% based on 3-methyl-2-pentene used), (iii) protection of 3,5-di(1-ethyl-1methylpropyl) phenol as an MOM ether by treating it with MOMCl and NaH in THF at rt (>99%), (iv) treatment of the resulting MOM ether with sec-BuLi in THF at -78°C followed by N,N-dimethylformamide at -78°C ∼ rt (96%), and (v) hydrolysis of the MOM-protected hydroxybenzaldehyde with 2-propanol saturated with HCl at rt (>99%)
42. Although we had reported that the relative reaction ratio between 7 and 8 is >12 (Ref. 9a), the present study revealed that it is 15
43. 6 but its oxidation was also carried out in chloroform-d
44. Irradiation was continued during the reaction. The role of photo-irradiation is twofold: (i) dissociation of the apicalnitrosyl ligand and (ii) acceleration of single electron transfer from Ru(III) species to molecular oxygen. The detailed mechanism of the reaction will be discussed elsewhere
45. Reaction could be carried out in 5 mmol scale in a round-bottomed flask (100 mL) with three halogen lamps (150 W). The reaction in larger scale needs a more potent light source, because the reaction mixture is colored brownish red due to the presence of Ru complexes