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Iron(III)‐Catalyzed 1,3‐Functional Group Transposition Reactions: Synthetic Protocol to Access 3‐Substituted Indoles
Author(s) -
Li DeYao,
Wei Yin,
Shi Min
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600037
Subject(s) - chemistry , indole test , functional group , yield (engineering) , phthalide , combinatorial chemistry , derivative (finance) , transposition (logic) , catalysis , organic chemistry , linguistics , materials science , philosophy , economics , financial economics , metallurgy , polymer
An iron(III)‐catalyzed 1,3‐dihydroisobenzofuran transferring reaction of indoles provides a practical synthetic protocol to access 3‐substituted indoles under mild conditions. This is the first example of a 1,3‐functional group transposition of a N ‐protected indole to give a 3‐substituted indole derivative in good yield. A plausible mechanism has been proposed on the basis of deuterium‐labeling and control experiments. Furthermore, after a simple oxidation, the obtained product could be easily transformed into 3‐phthalide indole, a drug candidate for treating Alzheimer′s disease.