Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents. Issue 41 (4th September 2017)

• Record Type: Journal Article
• Authors: Ma, Xinghua; Diane, Mohamed; Ralph, Glenn; Chen, Christine; Biscoe, Mark R.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 41(2017)
• Page Start: 12663
• Page End: 12667
• Publication Date: 2017-09-04
• Subjects: carbastannatrane -- fluorination -- halogenation -- Selectfluor -- stereospecificity; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201704672
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report the use of isolable primary and secondary alkylcarbastannatrane nucleophiles in site‐specific fluorination reactions. These reactions occur without the need for transition metal catalysis or in situ activation of the nucleophile. In the absence of the carbastannatrane backbone, alkyltin nucleophiles exhibit no activity towards fluorination. When enantioenriched alkylcarbastannatranes are employed, fluorination occurs predominately via a stereoinvertive mechanism to generate highly enantioenriched alkyl fluoride compounds. These conditions can also be extended to stereospecific chlorination, bromination, and iodination reactions. Abstract : Speed matters : Site‐specific fluorination reactions of isolable primary and secondary alkylcarbastannatrane nucleophiles occur fast, without the need for transition metal catalysis, or in situ activation of the nucleophile. The reaction conditions can also be extended to stereospecific chlorination, bromination, and iodination reactions.