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Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols

Caleb Karmel, Bijie Li and John F. Hartwig*

*Department of Chemistry, University of California, Berkeley, California 94720, United States, Email:

C. Karmel, B. Li, J. F. Hartwig, J. Am. Chem. Soc., 2018, 140, 1460-1470.

DOI: 10.1021/jacs.7b11964

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(Hydrido)silyl ethers, generated in situ by dehydrogenative coupling of tertiary alcohols with diethylsilane, undergo regioselective silylation at a primary C-H bond δ to the hydroxyl group in the presence of [(Xantphos)Rh(Cl)] as catalyst. Fleming-Tamao oxidation of the resulting 6-membered oxasilolanes provides 1,4-diols.

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reaction pathway

Key Words

Hydroxylation, Fleming-Tamao Oxidation

ID: J48-Y2018