search
Login Form

5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane

CAS 93253-73-7, Cat. No EN300-7867142
Reagent-precursor to organostannatranes

5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane
EN300-7867142

EnamineStore

The reagent is one of the most popular precursors to alkylstannatranes1, which is being used for sp3–sp2 coupling reactions2. It is solid, soluble in Et2O, THF, EtOAc, DCM, and hexane, and slightly soluble in MeCN, MeOH, and i-PrOH but insoluble in water. It is important to remember that organostannes are very toxic compounds and need to be handled with caution and in proper conditions. After the preparation of alkylstannane, they can be used in palladium-catalyzed allylic alkylation or cross-coupling3,4.

Synonyms: 1-aza-5-chloro-5-stannabicyclo[3.3.3]-undecane; 1-aza-5-stannabicyclo[3.3.3]undecane, 5-chloro- (9CI, ACI); 5-chloro-1-aza-5-stannabicyclo[3.3.3]undecane

Selected publications

  1. 5-Chloro-1-Aza-5-Stannabicyclo[3.3.3]Undecane.

    Mahoney S.; Fillion E. Encyclopedia of Reagents for Organic Synthesis 2013. DOI: 10.1002/047084289X.rn01600

  2. Ligand-Free Copper(I)-Mediated Cross-Coupling Reactions of Organostannanes with Sulfur Electrophiles.

    Zhu F.; Chen Z.; Walczak M. J Org Chem 2020, 85 (18), 11942–11951. DOI: 10.1021/acs.joc.0c01399

  3. Stereospecific Palladium‐Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.

    Wang C.; Ralph G.; Derosa J.; Biscoe M. Angewandte Chemie International Edition 2017, 56 (3), 856–860. DOI: 10.1002/anie.201609930

  4. Stereoretentive Pd-Catalysed Stille Cross-Coupling Reactions of Secondary Alkyl Azastannatranes and Aryl Halides.

    Li L.; Wang C.; Huang R.; Biscoe M. Nat Chem 2013, 5 (7), 607–612. DOI: 10.1038/nchem.1652

 

Contact Us