Nickel-catalyzed C(sp(2))-H/C(sp(3))-H oxidative coupling of indoles with toluene derivatives
| Title | Nickel-catalyzed C(sp(2))-H/C(sp(3))-H oxidative coupling of indoles with toluene derivatives |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Soni, V, Khake, SM, Punji, B |
| Journal | ACS Catalysis |
| Volume | 7 |
| Issue | 6 |
| Pagination | 4202-4208 |
| Date Published | JUN |
| Type of Article | Article |
| Abstract | Nickel-catalyzed oxidative C(sp(2))-H/C(sp(3))-H coupling of indoles with toluene derivatives is successfully achieved in the presence of 2-iodobutane as the oxidant. This method allows the selective C-2 benzylation of indoles with toluene derivatives over the alkylation with 2-iodobutane and permits the coupling of diversified indoles via the monochelation assistance. The reaction proceeded through a single-electron-transfer (SET) process, wherein both the C-H nickelation of indole and the C-H activation of toluene derivatives have a significant effect on the entire reaction rate. The synthetic utility of this nickel-catalyzed protocol is demonstrated by the facile removal of the directing group and by the convenient synthesis of the melatonin receptor antagonist Luzindole derivatives. |
| DOI | 10.1021/acscatal.7b01044 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 8.63 |
Divison category:
Chemical Engineering & Process Development