Palladium-Catalyzed Annulation of Internal Alkynes: Direct Access to π‑Conjugated Ullazines

A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino­[6,5,4,3-ija]­quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 12; pp. 2876 - 2879
Main Authors Wan, Danyang, Li, Xiaoyu, Jiang, Ruyong, Feng, Boya, Lan, Jingbo, Wang, Ruilin, You, Jingsong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2016
Amer Chemical Soc
Subjects
alkynes
carbon-hydrogen bond activation
catalytic activity
Chemistry
Chemistry, Organic
cyclization reactions
dyes
electronic equipment
moieties
palladium
Physical Sciences
quinolones
Science & Technology
HETEROARENES
DESIGN
SOLAR-CELLS
HYDROCARBONS
ARYLATION
BONDS
OXIDATIVE ANNULATION
C-H ACTIVATION
MOLECULES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.6b01182

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Summary:A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino­[6,5,4,3-ija]­quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C–H functionalization in the construction of organic optoelectronic materials.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b01182