Palladium-catalyzed desulfinylative C-C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters
Volla, CMRao; Dubbaka, SR; Vogel, P
| HERO ID | 4936161 |
|---|---|
| In Press | No |
| Year | 2009 |
| Title | Palladium-catalyzed desulfinylative C-C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters |
| Authors | Volla, CMRao; Dubbaka, SR; Vogel, P |
| Journal | Tetrahedron |
| Volume | 65 |
| Issue | 2 |
| Page Numbers | 504-511 |
| Abstract | 2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C-C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl acetoacetate. Neopentyl alk-2-ene sulfonates can also be used as electrophilic partners in desulfinylative allylic arylations and allylic alkylations. The regioselectivity of the allylic arylation and alkylation depends on the nature of the catalyst. With PdCl(2)(PhCN)(2), (E)-crotyl derivatives are formed in high regioselectivity using either 1-methylprop-2-ene- or (E)-but-2-enesulfonyl chloride. (C) 2008 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.tet.2008.11.007 |
| Wosid | WOS:000262797900010 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Allylic alkylation; Allylic arylation; Homogenous catalysis; Regioselective allylation; Palladium complexes; Sulfonate esters; Sulfonyl chlorides; Grignard reagents |