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Merck
CN

900403

Sigma-Aldrich

SLAP HydroPyrrolopyrazine Reagent

别名:

(S)-(1-((Trimethylsilyl)methyl)pyrrolidin-2-yl)methanamine

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About This Item

经验公式(希尔记法):
C9H22N2Si
分子量:
186.37
UNSPSC代码:
12352103
NACRES:
NA.22

表单

liquid

质量水平

密度

0.8846 g/mL

官能团

amine

储存温度

−20°C

应用

Silicon amine protocol (SLAP) reagents, in conjunction with aldehydes and ketones, form N-unprotected piperazines via photocatalytic cross-coupling with Ir[(ppy)2dtbbpy]PF6 (747769). Heteroaromatic, aromatic, and aliphatic aldehydes are well tolerated, as are structurally and stereochemically complex SLAP reagents. This product was introduced in collaboration with the Bode Research Group and provides a tin-free alternative to SnAP (tin amine protocol) reagents for piperazine synthesis.

象形图

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警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

177.8 °F

闪点(°C)

81 °C

法规信息

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Moritz K Jackl et al.
Organic letters, 19(17), 4696-4699 (2017-08-17)
Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic
Sheng-Ying Hsieh et al.
ACS central science, 3(1), 66-72 (2017-02-06)
Redox neutral photocatalytic transformations often require careful pairing of the substrates and photoredox catalysts in order to achieve a catalytic cycle. This can limit the range of viable transformations, as we recently observed in attempting to extend the scope of
Sheng-Ying Hsieh et al.
Organic letters, 18(9), 2098-2101 (2016-04-22)
Silicon amine protocol (SLAP) reagents for photocatalytic cross-coupling with aldehydes and ketones to form N-unprotected piperazines have been developed. This blue light promoted process tolerates a wide range of heteroaromatic, aromatic, and aliphatic aldehydes and structurally and stereochemically complex SLAP

实验方案

The expanding class of SLAP reagents provides access to saturated N-heterocycles and aliphatic aldehydes and ketones without additional reagents or the generation of toxic byproducts.

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