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Merck
CN

925446

Sigma-Aldrich

5-Vinylthianthrenium tetrafluoroborate

≥95%

别名:

Vinyl-TT

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About This Item

经验公式(希尔记法):
C14H11BF4S2
分子量:
330.17
MDL编号:
UNSPSC代码:
12352108
NACRES:
NA.22

质量水平

方案

≥95%

表单

powder

反应适用性

reaction type: C-C Bond Formation

mp

110-112 °C

官能团

thioether

储存温度

−20°C

SMILES字符串

[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 key

FXHBWPNFHMRFKM-UHFFFAOYSA-N

应用

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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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