All Photos(1)
Synonym(s):
2-((Bis(trimethylsilyl)methyl)thio)ethanamine
Empirical Formula (Hill Notation):
C9H25NSSi2
Assay
≥95%
form
suspension
density
0.9126
storage temp.
2-8°C
SMILES string
NCCSC([Si](C)(C)C)[Si](C)(C)C
Application
When used with aliphatic or aromatic aldehydes, this silicon amine protocol SLAP reagent enables the photomediated synthesis of thiomorpholines and thiazepanes. For photocatalytic cross-coupling with this SLAP Reagent, Ir[(ppy)2dtbbpy]PF6 (747769) is used with a recommended starting combination of Lewis acids Bi(OTf)3 (633305) and Cu(OTf)2 (283673) prior to subsequent substrate-specific optimization. This product was introduced in collaboration with the Bode Research Group and provides a tin-free alternative to SnAP (tin amine protocol) reagents and is well-suited for scale-up reactions.
Other Notes
- Technology Spotlight: SLAP Reagents for Piperazine Synthesis
- Silicon Amine Reagents for the Photocatalytic Synthesis of Piperazines from Aldehydes and Ketones
- Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents.
- Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
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Product No.
Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 2
WGK
WGK 3
Flash Point(F)
30.0 °F
Flash Point(C)
-1.11 °C
Regulatory Information
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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
Protocols
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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