Palladium-Catalyzed sp(3) C-H Nitration of 8-Methylquinolines

Palladium-Catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp(3) C-H bond activation. The resulting (nitromethyl)quinolines could be Selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)-methan...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 11; pp. 5973 - 5978
Main Authors Zhang, Wei, Ren, Shaobo, Zhang, Jian, Liu, Yunkui
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.06.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
REGIOSPECIFIC SYNTHESIS
ELECTROPHILIC REACTIONS
NITROALKANES
FUNCTIONAL-GROUPS
IPSO-NITRATION
NITRO
SINGLE BONDS
EFFICIENT
ARYLBORONIC ACIDS
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Summary:Palladium-Catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp(3) C-H bond activation. The resulting (nitromethyl)quinolines could be Selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)-methanamines by NaBH4 in the presence of a catalytic amount of NiCl2 center dot 6H(2)O.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00735