Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 12, Pages 4283-4285Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0496143
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From a screen of (cyanide)metal complexes, an improved catalyst for the cross silyl benzoin addition was discovered. Several M(CN)(3) complexes (M = Ce, Er, Sm, Y, Yb, La) were evaluated and lanthanum tricyanide was identified as the optimal catalyst. The catalyst, prepared in situ from LaCl3, effects the selective coupling of aryl and alkyl acylsilanes with aryl, heteroaryl, alpha,beta-unsaturated, and aliphatic aldehydes. The reactions occur at ambient temperature in less than 5 min to provide, depending on the workup, alpha-hydroxy or alpha-silyloxy ketones in 48-93% isolated yield.
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