Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters

Chowdhury, Sarwat; Standaert, Robert F.

doi:10.1021/acs.joc.6b01699

Title: Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters

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Abstract

Primary alcohols can be deoxygenated cleanly and in high yield by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it both simple and convenient.

Authors:

Chowdhury, Sarwat ^[1]; Standaert, Robert F. ^[2]

Univ. of Illinois, Chicago, IL (United States). Dept. of Chemistry
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Biosciences Division; Univ. of Tennessee, Knoxville, TN (United States). Dept. of Biochemistry and Cellular & Molecular Biology

Publication Date:: Thu Sep 15 00:00:00 EDT 2016

Research Org.:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE; Work for Others (WFO)

OSTI Identifier:: 1327565

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Organic Chemistry

Additional Journal Information:: Journal Volume: 81; Journal ID: ISSN 0022-3263

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; deoxygenation; phosphorus chemistry; green chemistry; reduction; organic synthesis

Citation Formats


                    Chowdhury, Sarwat, and Standaert, Robert F. Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters.  United States: N. p., 2016. 
Web.  doi:10.1021/acs.joc.6b01699.

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                    Chowdhury, Sarwat, & Standaert, Robert F. Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters.  United States.  https://doi.org/10.1021/acs.joc.6b01699

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                    Chowdhury, Sarwat, and Standaert, Robert F. Thu .  
"Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters".  United States.  https://doi.org/10.1021/acs.joc.6b01699.  https://www.osti.gov/servlets/purl/1327565.

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@article{osti_1327565,

  title        = {Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters},

  author       = {Chowdhury, Sarwat and Standaert, Robert F.},

  abstractNote = {Primary alcohols can be deoxygenated cleanly and in high yield by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it both simple and convenient.},

  doi          = {10.1021/acs.joc.6b01699},

  journal      = {Journal of Organic Chemistry},

  number       = ,

  volume       = 81,

  place        = {United States},

  year         = {Thu Sep 15 00:00:00 EDT 2016},

  month        = {Thu Sep 15 00:00:00 EDT 2016}

}

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https://doi.org/10.1021/acs.joc.6b01699

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