Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

Tetrahedron Letters

Volumn 48, Issue 7, 2007, Pages 1237-1240

  Uenishi, Jun'ichi ^a   Iwamoto, Takuya ^a   Ohmi, Masashi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; ALLYLSILANE DERIVATIVE; BROMINE DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; LEWIS ACID; METHYL GROUP; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DESILYLATION; PROTODESILYLATION; SYNTHESIS;

EID: 33846244710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.044     Document Type: Article

References (19)

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3. Protodesilylation as a side reaction, for example:. Schinzer D., Allagiannis C., and Wichmann S. Tetrahedron 44 (1988) 3851
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16. 4Cl, extraction with hexane and purification by silica gel column chromatography gave bisallylsilane 2
17. 3 and extracted with hexane. The crude product was purified by column chromatography on silica gel to give 4.
18. It should be noted that protodesilylation is a delicate reaction. Fine adjustment of reaction conditions for solvent and temperature are required in specific cases.
19. Over protodesilylation occurred.