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Volumn 47, Issue 16, 2008, Pages 3050-3053

Distannylations and silastannylations of in situ generated allenes

Author keywords

Allenes; Dimetalation; Hydrostannylation; Molybdenum; Palladium

Indexed keywords

CHEMICAL REACTIONS; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS;

EID: 53549084579     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705976     Document Type: Article
Times cited : (11)

References (59)
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    • Comparable reactions on alkynes: a) (Sn-Si): T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, U. Schneider, J. Org. Chem. 1987, 52, 4868-4874;
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    • The yields obtained in the hydrostannylation can be increased by running the reaction in an atmosphere of CO, probably because of a prolonged lifetime of the catalyst
    • The yields obtained in the hydrostannylation can be increased by running the reaction in an atmosphere of CO, probably because of a prolonged lifetime of the catalyst.
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    • For Pd-free β eliminations of α-hydroxyvinyl stannanes to allenes, see
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    • Unfortunately, propargyl acetate A could not be hydrostannylated in the presence of Pd, because the competing formation of allenyl-Pd complexes was faster.
    • Unfortunately, propargyl acetate A could not be hydrostannylated in the presence of Pd, because the competing formation of allenyl-Pd complexes was faster.
  • 49
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    • The regioselectivity towards the desired α-stannylated product in general is lower with Pd catalysts in comparison to the molybdenum catalyst MoBI3 see reference [14, and references therein
    • 3 (see reference [14], and references therein).
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    • No elimination was observed in the absence of palladium
    • No elimination was observed in the absence of palladium.
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    • This reaction was not optimized, owing to the high toxicity of the methylstannanes
    • This reaction was not optimized, owing to the high toxicity of the methylstannanes.
  • 56
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    • [5a] reported an inverse regioselectivity in the case of B-Si.
    • [5a] reported an inverse regioselectivity in the case of B-Si.
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    • The direct disilylation requires reaction temperatures of around 120°C (see reference [10]). The attempt to react 2a with hexamethyldisilane was unsuccessful.
    • The direct disilylation requires reaction temperatures of around 120°C (see reference [10]). The attempt to react 2a with hexamethyldisilane was unsuccessful.
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    • 4] result in a dramatic drop in yield.
    • 4] result in a dramatic drop in yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.