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Catalytic C‐2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles
Author(s) -
Lee Ju Young,
Ha Hyeri,
Bae Seri,
Han Inhyuk,
Joo Jung Min
Publication year - 2016
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.201600568
Subject(s) - chemistry , indole test , norbornadiene , synthon , ring (chemistry) , catalysis , acetylene , combinatorial chemistry , palladium , organic chemistry
We report a palladium‐catalyzed C‐2 allylation of indoles and subsequent cyclization of the allylated indoles. The electronic effects of chloro and ester groups that can be readily installed at the C‐3 position of indoles facilitated a highly efficient C–H allylation at the C‐2 position. The resulting 2‐allyl‐3‐chloroindoles were found to be suitable substrates for benzannulation reactions with alkynes and norbornadiene as an acetylene synthon. This approach, utilizing readily available indoles, allyl acetates, and norbornadiene, allows a rapid access to complex carbazoles.