SiGNa Chemistry: Reactions

Classic Method

Nitrogen is central to medicinally-oriented organic synthesis, therefore it is important to be able to protect and deprotect them throughout a synthesis. However, the most useful nitrogen protecting groups, like sulfonamides, which provide high crystallinity are extremely difficult to remove in high yield through simple non-toxic methods.

Classic #1
Classic #2

Diphenyl Sulfonamide Deprotection

N-Allylimidazole Deprotection

Problems

Requires highly toxic materials like sodium-mercury amalgam
Conditions utilize strong acids at high temperatures
Handling of alkali metals and liquid ammonia at cryogenic temperatures
Safety and economic issues due to special equipment and disposal needs

SiGNa's Method

Nitrogen deprotection using SiGNa materials effects clean desulfonation and deallylation utilizing a safe, smooth solution process. The SiGNa method improves yield and reaction conditions, provides milder conditions, and simplifies process purification.

Dep. #1
Dep. #2
Dep. #3

Diphenyl Sulfonamide Deprotection

N-Allylimidazole Deprotection

N-Tosyl Pyrrole Deprotection

Benefits

Provides a smooth solution process at room temperature
Highly selective allowing more options for substrate functionalization
No toxic (i.e. mercury) or hazardous (i.e. liquid ammonia) materials needed
No special equipment required for handling or processing

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