The polar effect on the regiochemistry of nucleophilic substitution of trifluoromethylated pi-allylpalladium complex
Okano, T; Matsubara, H; Kusukawa, T; Fujita, M
| HERO ID | 4936239 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | The polar effect on the regiochemistry of nucleophilic substitution of trifluoromethylated pi-allylpalladium complex |
| Authors | Okano, T; Matsubara, H; Kusukawa, T; Fujita, M |
| Journal | Journal of Organometallic Chemistry |
| Volume | 676 |
| Issue | 1-2 |
| Page Numbers | 43-48 |
| Abstract | Allylic nucleophilic substitution of trifluoromethyl-group substituted cinnamyl carbonate with diethyl malonate anion in the presence of palladium complex catalyst gave regio- and stereo selectively the S(N)2' product. The regiochemistry caused by the polar effect of trifluoromethyl group was opposite to the methylated cinnamyl substrate in a similar steric environment. The sterically more hindered mesityl and tert-butyl substrates than phenyl derivative also gave the products reacted at the more hindered sites. Although o-substituted substrates expecting intramolecular coordination to affect regiochemistry were examined, no alternative regioisomers were detected. (C) 2003 Elsevier Science B.V. All rights reserved. |
| Doi | 10.1016/S0022-328X(03)00262-6 |
| Wosid | WOS:000183589000005 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | pi-allylpalladium complexes; regiochemistry; trifluoromethyl group; alpha-acceptor |