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Preparation of an Indolylfulgimide‐Adamantane Linker Conjugate with Nitrile Anchoring Groups through Palladium‐Catalyzed Transformations
Author(s) -
Zarwell Sebastian,
Dietrich Steffen,
Schulz Christine,
Dietrich Paul,
Michalik Fabian,
RückBraun Karola
Publication year - 2009
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.200801199
Subject(s) - sonogashira coupling , chemistry , cyanation , linker , nitrile , palladium , phenylacetylene , conjugate , benzonitrile , adamantane , acetylene , catalysis , combinatorial chemistry , indole test , polymer chemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics , computer science , operating system
We report the preparation, through palladium‐catalyzed transformations, of the indolylfulgimide linker conjugate 1 , containing an adamantane core and nitrile anchoring groups. The ethynylene‐linker 12 for the final Sonogashira coupling was prepared through palladium‐mediated cyanation of an iodo‐substituted precursor with Zn(CN) 2 . The synthesis of the 6‐bromo‐substituted indolylfulgimide coupling partner 2 was accomplished in seven steps. Model studies using phenylacetylene and the 5‐bromo‐substituted indole 13 were conducted to find conditions that would prevent homocoupling of the ethynylene linker 12 in the final Sonogashira coupling step. The use of Pd(PhCN) 2 Cl 2 and [( t Bu) 3 PH]BF 4 in the presence of diisopropylamine, together with CuI as additive, proved to be most efficient. Finally, the photochromic properties of conjugate 1 and indolylfulgimide 2 were studied.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)