Amide‐Directed C−H Sodiation by a Sodium Hydride/Iodide Composite

A new protocol for amide‐directed ortho and lateral C−H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds. New direction: An amide‐di...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 23; pp. 6544 - 6547
Main Authors Huang, Yinhua, Chan, Guo Hao, Chiba, Shunsuke
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.06.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
amides
arenes
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
C−H activation
Intermediates
Iodides
Lithium
metalation
Physical Sciences
Science & Technology
Sodium
sodium hydride
Sodium hydrides
Sodium iodide
DEPROTONATION
amides
ORGANOSODIUM
ORGANOPOTASSIUM COMPOUNDS
2-INDANONES
metalation
sodium hydride
METHODOLOGY
C-H activation
IODIDE COMPOSITE
arenes
FRIES REARRANGEMENT
LITHIATION
ORTHO-METALATION
POLYSUBSTITUTED AROMATICS
C−H activation
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Summary:A new protocol for amide‐directed ortho and lateral C−H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds. New direction: An amide‐directed ortho and lateral C−H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds.
Bibliography:These authors contributed equally.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201702512