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Merck
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文件

925446

Sigma-Aldrich

5-Vinylthianthrenium tetrafluoroborate

≥95%

同義詞:

Vinyl-TT

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About This Item

經驗公式(希爾表示法):
C14H11BF4S2
CAS號碼:
分子量::
330.17
分類程式碼代碼:
12352108
NACRES:
NA.22

品質等級

化驗

≥95%

形狀

powder

反應適用性

reaction type: C-C Bond Formation

mp

110-112 °C

儲存溫度

−20°C

SMILES 字串

[F-][B+3]([F-])([F-])[F-].S1C=2C=CC=CC2[S+](C=C)C=3C=CC=CC13

InChI

1S/C14H11S2.BF4/c1-2-16-13-9-5-3-7-11(13)15-12-8-4-6-10-14(12)16;2-1(3,4)5/h2-10H,1H2;/q+1;-1

InChI 密鑰

FXHBWPNFHMRFKM-UHFFFAOYSA-N

應用

5-Vinylthianthrenium tetrafluoroborate is a crystalline, shelf-stable vinylating reagent developed by the Ritter Lab. Despite the great functionality of the vinyl group for diversification of target compounds, the selective installation of this moeity has remained challenging. 5-Vinylthianthrenium tetrafluoroborate can perform this otherwise challenging transformation with a broad scope of substrate, including the N-vinylation of heterocycles, vinylation of aryl boronic acids, and the annulation of cyclic and heterocyclic substrates. Additionally, this reagent can be used to enable palladium catalyzed cross-coupling reactions. The functionality of 5-vinylthianthrenium tetrafluoroborate enables the usage of vinyl groups as a versatile tool for further functionalization of many substrates and is a functional tool for many snythetic pathways.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


分析證明 (COA)

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Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation
Hartmann P, et al.
Nature Chemistry, 16, 380-388 (2024)
Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
Fabio Julia, et al
Journal of the American Chemical Society, 143, 33, 12992?12998-12992?12998 (2021)

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