Generation of 1,2-azaboretidines via reduction of ADC borane adducts
Braunschweig, H; Gackstatter, A; Kupfer, T; Scheller, T; Hupp, F; Damme, A; Arnold, N; Ewing, WC
| HERO ID | 2906716 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Generation of 1,2-azaboretidines via reduction of ADC borane adducts |
| Authors | Braunschweig, H; Gackstatter, A; Kupfer, T; Scheller, T; Hupp, F; Damme, A; Arnold, N; Ewing, WC |
| Volume | 6 |
| Issue | 6 |
| Page Numbers | 3461-3465 |
| Abstract | 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 MesBBr(2) 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. |
| Doi | 10.1039/c5sc01077b |
| Wosid | WOS:000354815600025 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Journal:CHEMICAL SCIENCE 2041-6520 |
| Is Public | Yes |