Allylation of carbonyl compounds mediated by nanometer-sized bismuth in water

Synlett

Volumn , Issue 7, 2004, Pages 1171-1174

  Xu, Xiaolan ^a   Zha, Zhenggen ^a   Miao, Qian ^a,b   Wang, Zhiyong ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Allylation; Aromatic; Carbonyl compounds; Stereoselectivity; Water

Indexed keywords

ALCOHOL; BISMUTH; CARBONYL DERIVATIVE; NANOPARTICLE; WATER;

ALLYLATION; ARTICLE; DEVICE; PARTICLE SIZE; STEREOCHEMISTRY;

EID: 2942726542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822924     Document Type: Article

References (29)

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16. 1H NMR. When necessary, purification was performed by flash column chromatography over silica gel.
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21. General procedure for the allylation of aldehydes with allyl bromide mediated by regular Bi in distilled water. To a suspension of bismuth powder (0.250 g, 1.2 mmol) and allyl bromide (0.18 mL, 2 mmol) in water was added benzaldehyde (0.11 mL, 1 mmol). The reaction mixture was stirred at r.t. and monitored by TLC. After 24 h, the mixture was filtered to remove the white precipitate and the filtrate was extracted with ether (3 x 15 mL). The combined organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography over silica gel, affording the corresponding homoallylic alcohols.
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23. 2O (2 mL). After the addition was completed, the reaction mixture was stirred continuously for 15 min, then benzaldehyde (0.11 mL, 1 mmol) and allyl bromide (0.18 mL, 2 mmol) were added. Then the reaction mixture was treated as described in ref. 10.
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25. See Figure 2.
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