Radical Metal-Free Borylation of Aryl Iodides

A simple metal-free borylation of aryl iodides mediated by a fluoride sp(2)-sp(3) diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 49; no. 21; pp. 4759 - 4768
Main Authors Pinet, Sandra, Liautard, Virginie, Debiais, Megane, Pucheault, Mathieu
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.11.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
metal-free borylation
ROOM-TEMPERATURE
pyridine
POTASSIUM TERT-BUTOXIDE
radical process
BOND FORMATION
AMINE-BORANE COMPLEXES
AROMATIC-AMINES
PALLADIUM-CATALYZED BORYLATION
BORINIC ACIDS
MILD CONDITIONS
cesium fluoride
BORON SOURCE
ARYLBORONIC PINACOL ESTERS
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Summary:A simple metal-free borylation of aryl iodides mediated by a fluoride sp(2)-sp(3) diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588431