Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using N‐Haloimides and Triphenylphosphine. Issue 33 (6th September 2021)

• Record Type: Journal Article
• Authors: Irving, Charles D.; Floreancig, Jack T.; Gasonoo, Makafui; Kelley, Alexandra S.; Laulhé, Sébastien
• Is Part Of: ChemistrySelect. Volume 6:Issue 33(2021)
• Page Start: 8874
• Page End: 8878
• Publication Date: 2021-09-06
• Subjects: Amine Precursors -- Deoxyamination -- Mitsunobu Reaction -- N-haloimides -- Triphenylphosphine; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202102296
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A deoxyamination methodology of activated and unactivated alcohols is presented. The reaction is mediated by phosphonium intermediates generated in situ from N ‐haloimides and triphenylphosphine. The protocol allows for the synthesis of phthalimide and amine derivatives in moderate to good yields at room temperature. A series of NMR experiments have provided insight into the reactive intermediates involved and the mechanism of this deoxyamination reaction. Abstract : Two deoxyamination methodologies of alcohols are presented. These reactions are mediated by phosphonium species generated in situ through the reaction of triphenylphosphine and N ‐haloimides. When the reaction is performed in presence of Cs2 CO3 as a base additive, the alcohol is transformed into the imide product, thereby emulating a Mitsunobu reaction without the need of azodicarboxylate activating agent. If external amine source is added, the alcohol is transformed into the secondary or tertiary amine product.