Stille-type cross-coupling between α-alkoxy(amino)stannanes and acyl chlorides affords α-hetero-substituted ketones in moderate to good yields when cocatalyzed by Pd and Cu(I) salts. The reaction is applicable to a wide range of tin compounds, especially those bearing α-electron-withdrawing groups such as benzoyloxy or acetyloxy, although some ethers (e.g., MOM) are also satisfactory. Aromatic acid chlorides give the best yields. Coupling of chiral α-alkoxystannanes, readily available by BINAL-H asymmetric reduction of acylstannanes, proceeds with retention of configuration.
|Original language||English (US)|
|Number of pages||5|
|Journal||Journal of the American Chemical Society|
|State||Published - Jan 1 1994|
ASJC Scopus subject areas
- Colloid and Surface Chemistry