Continuous flow synthesis of arylhydrazines via nickel/photoredox coupling of tert-butyl carbazate with aryl halides. Issue 93 (5th November 2020)

• Record Type: Journal Article
• Authors: Mata, Alejandro; Tran, Duc N.; Weigl, Ulrich; Williams, Jason D.; Kappe, C. Oliver
• Is Part Of: Chemical communications. Volume 56:Issue 93(2020)
• Page Start: 14621
• Page End: 14624
• Publication Date: 2020-11-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc06787c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We present the first nickel/photoredox coupling of (hetero)aryl halides with hydrazine derivatives, allowing access to valuable arylhydrazine intermediates in flow. Abstract : Nickel/photoredox catalyzed C–N couplings of hydrazine-derived nucleophiles provide a powerful alternative to Pd-catalyzed methods. This continuous-flow photochemical protocol, optimized using design of experiments, achieves these couplings in short residence times, with high selectivity. A range of (hetero)aryl bromides and chlorides are compatible and understanding of process stability/reactor fouling has been discerned.