Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we ac...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 23; pp. 9124 - 9128
Main Authors Zhang, Li, Jiao, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.06.2019
Amer Chemical Soc
Subjects
boron compounds
catalytic activity
Chemistry
Chemistry, Multidisciplinary
organochlorine compounds
Physical Sciences
pyridines
Science & Technology
ultraviolet radiation
METAL-FREE BORYLATION
HALIDES
TRANSITION
IODIDES
ACTIVATION
ELECTRON-TRANSFER
FREE REDUCTIVE CLEAVAGE
ALKOXY DIBORON REAGENTS
CATALYZED BORYLATION
BOND
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Summary:The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b00917