With DBU-activated N-bromophthalimide as potential N-sources to achieve P–N cross-coupling of P(O)–H compounds. Issue 26 (29th June 2016)

• Record Type: Journal Article
• Authors: Li, Yueju; Liang, Fushun
• Is Part Of: Tetrahedron letters. Volume 57:Issue 26(2016)
• Page Start: 2931
• Page End: 2934
• Publication Date: 2016-06-29
• Subjects: P–N cross-coupling -- P(O)–H compounds -- N-Bromophthalimide -- Aminating reagent -- DBU; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.076
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A metal-free P–N cross-coupling is developed. Halogen bonding activation by DBU is the driving force for the P–N cross-coupling. An ionic rather than a radical mechanism is proposed. N -Haloimides can be utilized as an aminating reagent. Abstract: We have demonstrated that N -haloimides can be utilized as an aminating reagent, in addition to the traditional brominating reagent. Herein, the P–N cross-coupling of P(O)–H compounds and N -bromophthalimide has been developed with the DBU activation strategy. The nitrogen source may arise from internal N -bromophthalimide itself (a self-immolating reagent) or external phthalimide derivatives (with NBS-DBU activation system). The reaction features broad phosphorous compounds scope, including H -phosphinates, H -phosphonates, and H -phosphine oxides, and short reaction time (less than 10 min). This method provides a simple, convenient, efficient, and green route toward phosphoramidates which are of biological importance under mild conditions.