3 years ago

Deprotonation of a Seemingly Hydridic Diborane(6) to Build a B−B Bond

Deprotonation of a Seemingly Hydridic Diborane(6) to Build a B−B Bond
Hendrik Budy, Hans-Wolfram Lerner, Matthias Wagner, Michael Bolte, Thomas Kaese
Deprotonation of the doubly arylene-bridged diborane(6) derivative 1H2 with (Me3Si)3CLi or (Me3Si)2NK gives the B−B σ-bonded species M[1H] in essentially quantitative yields (THF, room temperature; M=Li, K, arylene=4,4′-di-tert-butyl-2,2′-biphenylylene). With nBuLi as the base, the yield of Li[1H] drops to 20 % and the 1,1-bis(9-borafluorenyl)butane Li[2H] is formed as a side product (30 %). In addition to the 1,1-butanediyl fragment, the two boron atoms of Li[2H] are linked by a μ-H bridge. In the closely related molecule Li[3H], the corresponding μ-H atom can be abstracted with (Me3Si)3CLi to afford the B−B-bonded conjugated base Li2[3] (THF, 150 °C; 15 %). Li[1H] and Li[2H] were characterized by NMR spectroscopy and X-ray crystallography. Fluid identity: A B−B bond was formed through the deprotonation of a doubly arylene-bridged diborane(6) derivative. The reaction shows that organoboranes are not necessarily hydridic and paves the way for new access routes to electron-precise diboranes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702393

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