Iron‐Catalyzed Functionalization of 3‐Benzylideneindoline Through Tandem Csp2–Csp3 Bond Formation/Isomerization with π‐Activated Alcohols

A new synthetic protocol was developed for the selective synthesis of diverse 3‐substituted indoles through tandem carbon–carbon bond formation and isomerization of 3‐benzylidene‐1‐tosylindoline by direct use of alcohols as alkylating agents in the presence of catalytic FeCl3. This method is applica...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-01, Vol.2020 (1), p.61-65
Main Authors: Chanda, Rupsa, Chakraborty, Baitan, Rana, Gopal, Jana, Umasish
Format: Article
Language:English
Subjects:
3‐Substituted indoles
Alcohol
Alcohols
Alkylation
Bonding
Carbon
Cascade chemical reactions
Catalysis
C–C bond formation
Ferric chloride
Functional groups
Indoles
Iron
Iron chlorides
Isomerization
Substrates
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Summary:A new synthetic protocol was developed for the selective synthesis of diverse 3‐substituted indoles through tandem carbon–carbon bond formation and isomerization of 3‐benzylidene‐1‐tosylindoline by direct use of alcohols as alkylating agents in the presence of catalytic FeCl3. This method is applicable to a wide range of substrates containing varieties of functional groups. Direct use of alcohols, such as benzylic, allylic, and propargylic alcohols, as electrophiles and the use of non‐toxic iron catalyst makes this strategy attractive and environmentally benign. A plausible mechanism has also been proposed for this tandem reaction. An efficient and environmentally benign procedure for the synthesis of 3‐substituted indole derivatives using iron‐catalyzed direct substitution of alcohol with 3‐benzylidene‐1‐tosylindoline via tandem C–C bond formation and isomerization is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901181