Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2

For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel–Crafts type reactions with arenes via benzyl iodide inte...

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Published inJournal of organic chemistry Vol. 86; no. 3; pp. 3081 - 3088
Main Authors Lv, Fang, Xiao, Jing, Xiang, Junchun, Guo, Fengzhe, Tang, Zi-Long, Han, Li-Biao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
NUCLEOPHILES
ALCOHOLS
ACID
REDUCTIVE HALOGENATION
ARENES
FRIEDEL-CRAFTS ALKYLATION
BROMIDES
CYCLIZATION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.0c02850

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Summary:For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel–Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.0c02850