Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2‑a]quinolines

The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh­(III)-catalyzed C–H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo­[1,2-a]­quinoline structures. As illust...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 12; pp. 2936 - 2939
Main Authors Liu, Xingyan, Li, Xiaoyu, Liu, Hu, Guo, Qiang, Lan, Jingbo, Wang, Ruilin, You, Jingsong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.06.2015
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Quinolines - chemical synthesis
Quinolines - chemistry
Rhodium - chemistry
Science & Technology
FUNCTIONALIZATION
DECARBONYLATION
HETEROCYCLES
STRATEGY
ARYLATION
CATALYZED TANDEM SYNTHESIS
SALICYLALDEHYDES
INDOLES
ALKENYLATION
CARBOXYLIC-ACIDS
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Summary:The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh­(III)-catalyzed C–H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo­[1,2-a]­quinoline structures. As illustrative examples, a concise three-step synthesis of indolo­[1,2-a]­quinoline-based sensitizers is accomplished that exhibits the potential of C–H activation in the construction of organic optoelectronic materials.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01171