Organic Photoredox Catalysis for Pschorr Reaction: A Metal-Free and Mild Approach to 6H-Benzo[c]chromenes

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6 H -benzo[ c ]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed o...

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Bibliographic Details
Published inSynlett Vol. 29; no. 17; pp. 2311 - 2315
Main Authors He, Jing-Yao, Bai, Qi-Fan, Jin, Chengan, Feng, Gaofeng
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
4+2 BENZANNULATION
SERIES
VISIBLE-LIGHT PHOTOREDOX
PHOTOCATALYSIS
organic photoredox catalysis
C-H bond functionalization
FUNCTIONALIZATION
PHENANTHRENE SYNTHESIS
diazonium salts
Pschorr reaction
C-H ARYLATION
ARYL DIAZONIUM SALTS
benzochromenes
DERIVATIVES
RING-CLOSURE
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Summary:An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6 H -benzo[ c ]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed or generated in situ from the corresponding amines with t -BuONO. The process is amenable to gram-sale synthesis of 6 H -benzo[ c ]chromenes, which can be further transformed into both 6 H -benzo[ c ]chromen-6-ones through oxidation or to 6 H -benzo[ c ]chromen-6-amine through sp (3) C-H bond amination. The protocol provides an attractive route for the synthesis of a library of 6 H -benzo[ c ]chromes.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1610279