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Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp3 CH arylation and electrophilic aromatic cyclization

Title
Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp3 CH arylation and electrophilic aromatic cyclization
Authors
Park, H.Yoo, K.Jung, Byung HyuckKim, M.
DGIST Authors
Jung, Byung Hyuck
Issue Date
2018-04
Citation
Tetrahedron, 74(16), 2048-2055
Type
Article
Article Type
Article
Author Keywords
Transient directing groupsC-H activationsp(3) C-H arylationOne-pot synthesisAnthracenes
Keywords
METAL-ORGANIC FRAMEWORKBOND ACTIVATIONATOM ECONOMYC(SP(3))-H ARYLATIONALIPHATIC-KETONESNATURAL-PRODUCTSFUNCTIONALIZATIONCONSTRUCTIONDERIVATIVESCATALYSIS
ISSN
0040-4020
Abstract
The first direct synthesis of substituted anthracenes from o-tolualdehydes and aryl iodides via a Pd(II)-catalyzed C. H arylation using an alcohol-bearing transient directing group and subsequent AgOTf-assisted electrophilic aromatic cyclization is described. New transient directing groups consisting of amino acids and amino alcohols enhanced the reactivity, and the C. H arylation was complete in 12 h at 90 °C. By simply changing the silver salt to silver triflate, the one-pot synthesis of anthracene derivatives was carried out using the present reaction conditions. © 2018 Elsevier Ltd.
URI
http://hdl.handle.net/20.500.11750/6142
DOI
10.1016/j.tet.2018.03.006
Publisher
Elsevier Ltd
Related Researcher
  • Author Jung, Byunghyuck Asymmetric Organic Synthesis and Drug Synthesis Laboratory
  • Research Interests Organic Synthesis; Organo-transition metal chemistry; Catalytic Asymmetric Synthesis; Synthetic Methodologies; Synthesis of Natural Products and Drugs
Files:
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Collection:
School of Undergraduate Studies1. Journal Articles


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