Organic Letters
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benzylic C−H bond alkylation. As to 7, the diphenylmethyl is a
considerably bulky group, which results in the regiospecific
nucleophilic attack of C5 in 7. Although the dearomatization
intermediate 8 can be delivered smoothly, the following 1,5-
sigmatropic alkyl shift cannot proceed further due to the
significant steric hindrance of diphenymethyl group of 8.
In conclusion, we have developed an efficient protocol for
the formal benzylic C−H bond functionalization of 2,5-
dialkylfuran derivatives with ferrocenyl alcohols as alkylation
reagents, which features chemo- and regiospecificity, mild
conditions, and environmental benignity. For the first time, the
inert benzylic C−H bond of π-electron-rich heteroaromatic
2,5-dialkylfuran was conveniently alkylated to afford the
potentially useful hybrids of ferrocene and 2,5-DMF under
metallic catalyst-free conditions at room temperature.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
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Photoassisted Access to Complex Spiro-Poly-Heterocycles. Angew.
Chem., Int. Ed. 2015, 54, 11516.
Experimental procedures and characterization data for
all of the products (PDF)
AUTHOR INFORMATION
Corresponding Authors
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ORCID
(9) Ghosh, A. K.; Brindisi, M. Achmatowicz Reaction and its
Application in the Syntheses of Bioactive Molecules. RSC Adv. 2016,
6, 111564.
Notes
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by a chiral transient directing group. Chem. Commun. 2018, 54, 689.
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(14) Theodossiou, T. A.; Goncalves, A. R.; Yannakopoulou, K.;
Skarpen, E.; Berg, K. Photochemical internalization of tamoxifens
transported by a ″Trojan-horse″ nanoconjugate into breast-cancer cell
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Palladium-Catalyzed Transformations of Alkyl C-H Bonds. Chem. Rev.
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The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful to the National Natural Science Foundation of
China (21702117, 21776148) and the Natural Science
Foundation of Shandong Province (ZR2017BB005,
ZR2016BM07) as well as the Key Research & Development
Program of Shandong Province (2018GSF118224). Financial
support from the Talents of High Level Scientific Research
Foundation (6631115015, 6631110309, 6651118009) and
Central Laboratory of Qingdao Agricultural University for
NMR determination are also gratefully acknowledged.
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