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Iron‐Catalyzed Functionalization of 3‐Benzylideneindoline Through Tandem Csp 2 –Csp 3 Bond Formation/Isomerization with π‐Activated Alcohols
Author(s) -
Chanda Rupsa,
Chakraborty Baitan,
Rana Gopal,
Jana Umasish
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901181
Subject(s) - chemistry , isomerization , electrophile , catalysis , allylic rearrangement , tandem , surface modification , combinatorial chemistry , organic chemistry , cyclopropanation , cascade reaction , materials science , composite material
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 FeCl 3 . 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.