Spirocarbocycle Synthesis from Chloromethylarenes via Transition-Metal-Catalyzed Allylative Dearomatization and Ring Closure Metathesis

A strategy for the synthesis of spirocarbocycles by using chloromethyl arenes as starting materials is described in this paper. The palladium-catalyzed allylative dearomatization and the subsequent ruthenium-catalyzed ring closure metathesis proceeded smoothly under mild conditions to produce the co...

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Published inJournal of organic chemistry Vol. 87; no. 12; pp. 8229 - 8236
Main Authors Hu, Yanzhao, Zhang, Sheng, Yu, Xiaoqiang, Feng, Xiujuan, Yamaguchi, Masahiko, Bao, Ming
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 17.06.2022
American Chemical Society (ACS)
Amer Chemical Soc
Subjects
aromatic hydrocarbons
Catalysis
chemical reactions
Chemistry
Chemistry, Organic
Cyclization
methodology
organic chemistry
Palladium
Physical Sciences
Ruthenium
Science & Technology
REACTIVITY
ACTIVATION
REGIOSELECTIVE ALLYLATION
FACILE
ANNULATION
CONSTRUCTION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.2c00651

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Summary:A strategy for the synthesis of spirocarbocycles by using chloromethyl arenes as starting materials is described in this paper. The palladium-catalyzed allylative dearomatization and the subsequent ruthenium-catalyzed ring closure metathesis proceeded smoothly under mild conditions to produce the corresponding spirocarbocycle products with moderate to high yields. Benzene-ring-, naphthalene-ring-, and anthracene-ring-containing substrates can be easily transformed into spirocarbocycles by using the proposed method.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.2c00651