In:
European Journal of Organic Chemistry, Wiley, Vol. 2009, No. 13 ( 2009-05), p. 2088-2095
Abstract:
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)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2009:13
DOI:
10.1002/ejoc.200801199
Language:
English
Publisher:
Wiley
Publication Date:
2009
detail.hit.zdb_id:
1475010-7
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