Stereospecific palladium/copper cocatalyzed cross-coupling of α-alkoxy- and α-aminostannanes with acyl chlorides

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

Research output: Contribution to journalArticle

15 Citations (Scopus)

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)
JournalJournal of the American Chemical Society
Volume116
Issue number1
StatePublished - Jan 12 1994

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Bearings (structural)
Tin compounds
Palladium
Ketones
Carboxylic acids
Chlorides
Copper
Ethers
Tin Compounds
Salts
Electrons
Acids
alkoxyl radical

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereospecific palladium/copper cocatalyzed cross-coupling of α-alkoxy- and α-aminostannanes with acyl chlorides. / Ye, Jianhua; Bhatt, Rama K.; Falck, J. R.

In: Journal of the American Chemical Society, Vol. 116, No. 1, 12.01.1994.

Research output: Contribution to journalArticle

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AB - 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.

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