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1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry

Tang, Connie ; Liang, Quiming ; Jupp, Andrew R. ; Johnstone, Timothy C. ; Neu, Rebecca C. ; Song, Datong ; Grimme, Stefan ; Stephan, Douglas W.

Angewandte Chemie, 2017-12, Vol.129 (52), p.16815-16819 [Peer Reviewed Journal]

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Title:
1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry
Author: Tang, Connie ; Liang, Quiming ; Jupp, Andrew R. ; Johnstone, Timothy C. ; Neu, Rebecca C. ; Song, Datong ; Grimme, Stefan ; Stephan, Douglas W.
Subjects: Addukte ; Borane ; Chemistry ; Diphenyldiazomethan ; Hydroboration ; Hydroborierungen ; Stickstoff
Is Part Of: Angewandte Chemie, 2017-12, Vol.129 (52), p.16815-16819
Description: Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 and generates Ph2CB(C6F5)3. DFT computations reveal that formation of Ph2CN2B(C6F5)3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture. N‐N verbrückt: Diphenyldiazomethan reagiert mit HB(C6F5)2 und B(C6F5)3 unter 1,1‐Hydroborierung bzw. Adduktbildung. N2‐Freisetzung aus dem Addukt Ph2CN2B(C6F5)3 liefert das Diphenylcarben‐Boran‐Addukt. Rechnungen zufolge ist die N2‐Aufnahme thermodynamisch günstig, obwohl die Bildung des Carben‐Boran‐Addukts exotherm ist.
Publisher: Weinheim: Wiley Subscription Services, Inc
Language: English

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