1, 1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry. (5th December 2017)

• Record Type: Journal Article
• Authors: Tang, Connie; Liang, Quiming; Jupp, Andrew R.; Johnstone, Timothy C.; Neu, Rebecca C.; Song, Datong; Grimme, Stefan; Stephan, Douglas W.
• Is Part Of: Angewandte Chemie. Volume 129:Number 52(2017)
• Page Start: 16815
• Page End: 16819
• Publication Date: 2017-12-05
• Subjects: Addukte -- Borane -- Diphenyldiazomethan -- Hydroborierungen -- Stickstoff; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201710337
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Diphenyldiazomethane reacts with HB(C6 F5 )2 and B(C6 F5 )3, resulting in 1, 1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2 CN2 BH(C6 F5 )2 . The highly sensitive adduct Ph2 CN2 (B(C6 F5 )3 ) liberates N2 and generates Ph2 CB(C6 F5 )3 . DFT computations reveal that formation of Ph2 CN2 B(C6 F5 )3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture.