Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation

Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis­(pinacolato)­diboron as the starting materials, fac-Ir­(ppy)3 as the photocatalyst, and corresponding ar...

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Published inOrganic letters Vol. 18; no. 20; pp. 5248 - 5251
Main Authors Jiang, Min, Yang, Haijun, Fu, Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.10.2016
Amer Chemical Soc
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Abstract Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis­(pinacolato)­diboron as the starting materials, fac-Ir­(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
AbstractList Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)(3) as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy) as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)₃ as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis­(pinacolato)­diboron as the starting materials, fac-Ir­(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
Author Jiang, Min
Yang, Haijun
Fu, Hua
AuthorAffiliation Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry
Tsinghua University
AuthorAffiliation_xml – name: Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry
– name: Tsinghua University
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  fullname: Yang, Haijun
– sequence: 3
  givenname: Hua
  surname: Fu
  fullname: Fu, Hua
  email: fuhua@mail.tsinghua.edu.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/27690142$$D View this record in MEDLINE/PubMed
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Keywords METAL-FREE BORYLATION
PALLADIUM-CATALYZED BORYLATION
ROOM-TEMPERATURE
CROSS-COUPLING REACTIONS
BOND FUNCTIONALIZATION
SYNTHETIC APPLICATIONS
C-H BORYLATION
ALKOXY DIBORON REAGENTS
AROMATIC-SUBSTITUTION
ARYLBORONIC ACIDS
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Snippet Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use...
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SubjectTerms chemical structure
Chemistry
Chemistry, Organic
esters
hydroxylation
organic halogen compounds
phenols
photocatalysts
Physical Sciences
redox reactions
Science & Technology
Title Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation
URI http://dx.doi.org/10.1021/acs.orglett.6b02553
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000386187300016
https://www.ncbi.nlm.nih.gov/pubmed/27690142
https://www.proquest.com/docview/1835518786
https://www.proquest.com/docview/2020872491
Volume 18
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