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A Tandem “On‐Palladium” Heck–Jeffery Amination Route Toward the Synthesis of Functionalized Indole‐2‐carboxylates
Author(s) -
McNulty James,
Keskar Kunal
Publication year - 2011
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.201101072
Subject(s) - chemistry , amination , intramolecular force , heck reaction , palladium , indole test , tandem , annulation , organic chemistry , combinatorial chemistry , catalysis , composite material , materials science
A direct synthesis of functionalized indole‐2‐carboxylates involving a Pd II ‐catalyzed annulation of ortho ‐iodoanilines onto a vinyl ether is described. The reaction mechanism is shown to be distinct from a stepwise Heck, intramolecular amination pathway, likely involving a tandem “on‐palladium” Heck–Jeffery amination process incorporating a novel intramolecular amination step.
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