Stereospecific Palladium/Copper Cocatalyzed Cross-Coupling of α-Alkoxy- and α-Aminostannanes with Acyl Chlorides

J. Ye, R. K. Bhatt, J R Falck

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104 Scopus citations

Abstract

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 languageEnglish (US)
Pages (from-to)1-5
Number of pages5
JournalJournal of the American Chemical Society
Volume116
Issue number1
DOIs
StatePublished - Jan 1 1994

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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