Direct benzylation and allylic alkylation in high-temperature water without added catalysts

Tetrahedron Letters

Volumn 51, Issue 14, 2010, Pages 1847-1851

  Hirashita, Tsunehisa ^a   Kuwahara, Sho ^a   Okochi, Sota ^a   Tsuji, Makoto ^a   Araki, Shuki ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AROMATIC COMPOUND; BENZYL ALCOHOL; ELECTROPHILE;

ALKYLATION; ARTICLE; BENZYLATION; HIGH TEMPERATURE;

EID: 77449161619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.112     Document Type: Article

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48. General experimental procedure: All reactions were carried out in ion-exchanged water (<0.08 mS/cm), which was obtained by an ORGANO PURE LITE PRB-002A. The autoclave was purchased from Shikokurika Co., Ltd. Representative procedure for reaction screening (Table 2, entry 2): A mixture of benzhydrol (0.18 g, 1.0 mmol), 1-methylindole (0.15 mL, 1.2 mmol), and ion-exchanged water (15 mL) was introduced into an autoclave with a volume filling factor of 50%. The autoclave was heated at 220 °C in an electric drier for 6 h. After the reactor was cooled down to room temperature, the product was extracted with ether. The organic solution was washed with brine and concentrated under reduced pressure giving a crude product (321 mg), from which excess 1-methylindole was removed by distillation (150 °C, 20 mmHg) to afford 3-(1,1-diphenylmethyl)-1-methylindole (8ba, 291 mg, 98%).