Intramolecular hydroboration of unsaturated phosphine boranes
Shapland, P; Vedejs, E
| HERO ID | 5416727 |
|---|---|
| In Press | No |
| Year | 2004 |
| Title | Intramolecular hydroboration of unsaturated phosphine boranes |
| Authors | Shapland, P; Vedejs, E |
| Journal | Journal of Organic Chemistry |
| Volume | 69 |
| Issue | 12 |
| Page Numbers | 4094-4100 |
| Abstract | Homoallylic phosphine boranes undergo intramolecular hydroboration upon activation by triflic acid. The reaction occurs via an intermediate B-trifluorosulfonyloxyborane complex such as 15, followed by S(N)1-like or S(N)2-like displacement of the triflate leaving group, apparently leading to the formation of a four-center transition state. In the case of trisubstituted double bonds, as in the substrates 29 and 32, ionic hydrogenation of the alkene competes with internal hydroboration. |
| Doi | 10.1021/jo040125c |
| Pmid | 15176834 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |