An Organic Intermolecular Dehydrogenative Annulation Reaction

The discovery of a direct method for the synthesis of three-ring heterocyclic carbazoles from unactivated arenes and anilides by a metal-free (organic) intermolecular dehydrogenative annulation reaction under ambient laboratory conditions is reported. Iodine­(III) was used as the sole reagent either...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 8; pp. 2006 - 2009
Main Authors Maiti, Saikat, Achar, Tapas Kumar, Mal, Prasenjit
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.04.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H BOND ACTIVATION
PALLADIUM
AMINATION
SIMPLE ANILINES
HETEROCYCLES
ARENES
CONSTRUCTION
IODINE(III)
OXIDATIVE ANNULATION
CARBAZOLES
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Summary:The discovery of a direct method for the synthesis of three-ring heterocyclic carbazoles from unactivated arenes and anilides by a metal-free (organic) intermolecular dehydrogenative annulation reaction under ambient laboratory conditions is reported. Iodine­(III) was used as the sole reagent either stoichiometrically from inexpensive phenyliodine diacetate or organocatalytically by in situ generation from PhI–mCPBA. In a single step, three C­(sp2)–H bonds and one N­(sp3)–H bond are functionalized from two different arenes for tandem C–C and C–N bond formation reactions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00562