A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines. Issue 3 (17th January 2018)

• Record Type: Journal Article
• Authors: Gill, Daniel M.; Iveson, Matthew; Collins, Ian; Jones, Alan M.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 3(2018)
• Page Start: 238
• Page End: 242
• Publication Date: 2018-01-17
• Subjects: Mitsunobu -- Cyclodehydration -- Nucleophilic aromatic substitution -- Intramolecular -- Cyclisation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.12.017
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An unexpected Mitsunobu route to N -arylated azacycles. Mitsunobu cyclodehydration versus intramolecular cyclisation investigated. Reaction scope, ring size, steric and p Ka effects studied in model systems. Abstract: The scope of an unexpected Mitsunobu cyclisation to prepare N -arylated F sp 3 -enriched azacycles was investigated. In the current study, we have identified whether a p Ka-dependent Mitsunobu cyclodehydration or a p Ka-independent Mitsunobu intra molecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intra molecular nucleophilic displacement was determined to be the dominant pathway.