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Literature DB >> 15479050

Radical deoxygenation of hydroxyl groups via phosphites.

Abstract

A highly efficient, two-step sequence method for the deoxygenation of hydroxyl groups has been developed. The method involves the preparation of the 2-(2-iodophenyl)ethyl methyl phosphite derivative of an alcohol using methyl dichlorophosphite and 2-(2-iodophenyl)ethanol. Treatment of the phosphite intermediate with (n-Bu)3SnH/AIBN in refluxing benzene cleanly produces the deoxygenation product of the original alcohol.

Entities: Chemical

Year: 2004 PMID： 15479050 DOI： 10.1021/ja0462777

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

1. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Authors: Peter A Jordan; Scott J Miller
Journal: Angew Chem Int Ed Engl Date: 2012-02-08 Impact factor: 15.336

Review 2. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors: Christopher R Shugrue; Scott J Miller
Journal: Chem Rev Date: 2017-06-05 Impact factor: 60.622

3. Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation.

Authors: Johnny Z Wang; Holt A Sakai; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2022-07-19 Impact factor: 16.823

4. Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp³ C-O Bonds in Cyclic Acetals.

Authors: Ciro Romano; Laura Talavera; Enrique Gómez-Bengoa; Ruben Martin
Journal: J Am Chem Soc Date: 2022-06-24 Impact factor: 16.383

Radical deoxygenation of hydroxyl groups via phosphites.

1. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Review 2. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

3. Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation.

4. Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp³ C-O Bonds in Cyclic Acetals.

Review 5. Chemo- and site-selective derivatizations of natural products enabling biological studies.

6. Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis.

7. Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium.

Radical deoxygenation of hydroxyl groups via phosphites.

1. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Review 2. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

3. Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation.

4. Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C-O Bonds in Cyclic Acetals.

Review 5. Chemo- and site-selective derivatizations of natural products enabling biological studies.

6. Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis.

7. Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium.

4. Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp³ C-O Bonds in Cyclic Acetals.