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Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters

Sarwat Chowdhury and Robert F. Standaert*

*Biosciences Division, Oak Ridge National Laboratory, PO Box 2008, Oak Ridge, Tennessee 37831-6445, United States, Email: standaertrfornl.gov

S. Chowdhury, R. F. Standaert, J. Org. Chem., 2016, 81, 9957-9963.

DOI: 10.1021/acs.joc.6b01699 (free Supporting Information)


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Abstract

Primary alcohols can be deoxygenated cleanly and in good yields by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in THF at room temperature. Primary alcohols can selectively be reduced in the presence of secondary alcohols. An additional one pot two-step process makes the process simple and convenient.

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Key Words

deoxygenations, lithium triethylborohydride


ID: J42-Y2016