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Literature DB >> 31613033

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols.

Jingjing Wu¹, Robin M Bär¹, Lin Guo¹, Adam Noble¹, Varinder K Aggarwal¹.

Abstract

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton-McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

Entities: Chemical

Keywords: boronic esters; borylation; deoxygenation; photochemistry; radical reactions

Year: 2019 PMID： 31613033 DOI： 10.1002/anie.201910051

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

12 in total

1. Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.

Authors: Stavros K Kariofillis; Benjamin J Shields; Makeda A Tekle-Smith; Michael J Zacuto; Abigail G Doyle
Journal: J Am Chem Soc Date: 2020-04-10 Impact factor: 15.419

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols.

1. Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.

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

3. Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.

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

5. Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates.

6. Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes.

7. Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis.

8. A donor-acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids.

9. Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

10. Generation of non-stabilized alkyl radicals from thianthrenium salts for C-B and C-C bond formation.