Samarium(II) iodide solution

Application

Samarium(II) iodide solution (SmI₂) can be used as a reagent in the synthesis of:

• Benzannulated pyrrolizidines and indolizidines by SmI₂-induced cyclizations of indole derivatives.
• Chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted oxazolidinones through asymmetric Reformatsky type reaction.
• γ-Aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling reaction.

It can also be used in:

• Reduction of conjugated double and triple bonds into alkenes using SmI₂/H₂O/amine mixtures.
• Conversion of β-hydroxyketones into 1,3-diols by SmI₂/H₂O/Et₃N.
• Selective reduction of 6-membered lactones to the corresponding diols/triols using SmI₂-H₂O reagent system.

SmI₂ is an effective single-electron reducing agent for the promotion of ketone-olefin, ketyl aryl cyclizations, and pinacol coupling reactions under mild conditions. Often both intramolecular and intermolecular couplings proceed in a highly stereoselective fashion. It is also used in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

UPC:

51442437

Weight:

1.00 Ounces

HazmatClass:

No

Quantity:

25

Unit of Measurement:

ML

WeightUOM:

LB

MPN:

3471

CAS Number:

32248-43-4