Single-Electron Transmetalation: An Enabling Technology for Secondary Alkylboron Cross-Coupling

Single-electron-mediated alkyl transfer affords a novel mechanism for trans­metal­ation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyl­trifluoro­borates with an array of aryl bromides mediated by an Ir photo­redox catalyst...

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Published inJournal of the American Chemical Society Vol. 137; no. 6; pp. 2195 - 2198
Main Authors Primer, David N, Karakaya, Idris, Tellis, John C, Molander, Gary A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.02.2015
Amer Chemical Soc
Subjects
Boron - chemistry
Chemistry
Chemistry, Multidisciplinary
Electrons
Metals - chemistry
Physical Sciences
Science & Technology
NUCLEOPHILES
ACID
C-N
LIGHT
ESTERS
CHLORIDES
ARYL
PHOTOREDOX CATALYSIS
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Summary:Single-electron-mediated alkyl transfer affords a novel mechanism for trans­metal­ation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyl­trifluoro­borates with an array of aryl bromides mediated by an Ir photo­redox catalyst and a Ni cross-coupling catalyst.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja512946e