Generation of 1,2-azaboretidines via reduction of ADC borane adducts.

نویسندگان

  • H Braunschweig
  • A Gackstatter
  • T Kupfer
  • T Scheller
  • F Hupp
  • A Damme
  • N Arnold
  • W C Ewing
چکیده

Reaction of the acyclic (diamino)carbene (ADC) :C(NiPr2)2 (1) with different dihaloboranes of the type RBX2 (R = Mes, Dur; X = Cl, Br) smoothly afforded a novel class of ADC-stabilized borane adducts. For MesBBr2 however, the reaction did not stop at the adduct level, but an uncommon rearrangement process occurred, which eventually resulted in the formation of a 5-membered boracycle after elimination of mesitylene. Chemical reduction of the ADC borane adducts by KC8 selectively yielded air stable 1,2-azaboretidines. Detailed DFT studies suggest a reduction mechanism involving a highly reactive borylene intermediate, which is converted into the boracycles via a rearrangement/C-H activation sequence.

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عنوان ژورنال:
  • Chemical science

دوره 6 6  شماره 

صفحات  -

تاریخ انتشار 2015