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Manganese Chloride as an Efficient Catalyst for Selective Transformations of Indoles in the Presence of a Keto Carbonyl Group
Author(s) -
Li Minghao,
Yang Jie,
Gu Yanlong
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100211
Subject(s) - chemistry , dihydropyran , indole test , catalysis , manganese , electrophile , alcohol , medicinal chemistry , chloride , organic chemistry , nucleophile , alkoxy group , acetyl chloride , alkyl
Catalysis by manganese chloride tetrahydrate was found to be effective for the selective transformation of indoles, with which the desired acid‐catalyzed reaction could be promoted and, at the same time, a side reaction that also needs assistance of acid, the electrophilic reaction of indole with the co‐existing keto carbonyl group, does not occur. Some acid‐catalyzed reactions, such as the ring‐opening reaction of 2‐alkoxy‐3,4‐dihydropyran with indole, and transesterification of β‐keto ester with an alcohol that contains a C‐3 unsubstituted indole fragment, could be performed smoothly by using manganese chloride as catalyst. A new multicomponent reaction of indole, 3,4‐dihydropyran and β‐keto ester was also developed with catalysis by manganese chloride.