Palladium‐Catalyzed Benzofulvenation of o‐Arylanilines through C−H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene

We report the first example of Pd(II)‐catalyzed highly step‐ and atom‐economical benzofulvenation through free amine‐directed ortho C−H bond activation of o‐arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o‐arylaniline subs...

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Published inAdvanced synthesis & catalysis Vol. 361; no. 4; pp. 683 - 689
Main Authors Raju, Selvam, Hsiao, Huan‐Chang, Thirupathi, Selvakumar, Chen, Pei‐Ling, Chuang, Shih‐Ching
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.02.2019
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Subjects
Activation
benzofulvene
Chemistry
Chemistry, Applied
Chemistry, Organic
C−H bond activation
diphenylacetylene
Fluorescence
Hydrogen bonds
o-arylaniline
Oxidation
Palladium
Physical Sciences
Science & Technology
Substrates
ANNULATION
o-arylaniline
C-H bond activation
INTERNAL ALKYNES
IMINOQUINONE
CYCLOADDITION
CYCLIZATIONS
benzofulvene
ENEDIYNES
diphenylacetylene
palladium
C(SP)-H
DERIVATIVES
ACCESS
ALKENYLATION
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Summary:We report the first example of Pd(II)‐catalyzed highly step‐ and atom‐economical benzofulvenation through free amine‐directed ortho C−H bond activation of o‐arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o‐arylaniline substrates through C−H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics.
Bibliography:ObjectType-Article-1
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801352