Issue in Honor of Prof. Enrique Meléndez ARKIVOC 2004 (iv) 109-129
ISSN 1424-6376 Page 109
©
ARKAT USA, Inc
15-Membered triolefinic macrocycles,
their coordination chemistry with transition metals, and
the catalytic properties of their palladium metal complexes.
A review
Marcial Moreno-Mañas,*
a
Roser Pleixats,
a
Anna Roglans,
b
Rosa M. Sebastián,
a
and Adelina Vallribera
a
a
Department of Chemistry, Universitat Autònoma de Barcelona, Cerdanyola, 08193-Barcelona,
Spain
b
Department of Chemistry, Universitat de Girona, 17071-Girona, Spain
E-mail: marcial.moreno@uab.es
Dedicated to Professor Enrique Meléndez on occasion of his retirement
(received 06 Sep 03; accepted 12 Jan 04; published on the web 22 Jan 04)
Abstract
(E,E,E)-1,6,11-Tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,11-trienes, 1, are prepared
from arenesulfonamides and trans-1,4-dibromo-2-butene. Macrocycles 1 coordinate
palladium(0), platinum(0), and silver(I), and the palladium complexes are useful and reutilizable
catalysts or precatalysts in Suzuki cross-couplings, butadiene telomerizations, hydroarylation of
alkynes, and in the Heck reaction. Structurally related macrocycles are also available by similar
synthetic procedures.
Keywords: Alkene ligands, macrocycles, heterocycles, olefin complexes, catalysis
Contents
1. Introduction
2. Preparation of compounds
2.1 Preparation of 15-membered macrocycles
2.2 Preparation of metal complexes
3. Structure and spectroscopy
4. Catalysis
5. Related macrocycles
6. Concluding remarks