Calix[4]arene‐Supported  N ‐Heterocyclic Carbene Ligands as Catalysts for Suzuki Cross‐Coupling Reactions of Chlorotoluene | Zendy

Frank Markus | Zendy; Maas Gerhard | Zendy; Schatz Jürgen | Zendy

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Calix[4]arene‐Supported N ‐Heterocyclic Carbene Ligands as Catalysts for Suzuki Cross‐Coupling Reactions of Chlorotoluene

Author(s) -

Frank Markus,

Maas Gerhard,

Schatz Jürgen

Publication year - 2004

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.200300542

Subject(s) - chemistry , carbene , palladium , calixarene , catalysis , suzuki reaction , toluene , salt (chemistry) , chelation , polymer chemistry , medicinal chemistry , crystal structure , coupling reaction , organic chemistry , molecule

Stable N ‐heterocyclic carbenes are generated starting from 5,17‐(bis‐imidazolium)‐substituted calix[4]arenes. Addition of Pd(OAc) 2 to these carbenes leads to macrocyclic cis ‐palladium chelate complexes in which the distal bridging of the upper rim leads to a strong distortion of the calix[4]arene skeleton which was proven by X‐ray crystal structure determination. Using an in‐situ catalytic system consisting of a calixarene‐imidazolium salt, Cs 2 CO 3 as a base and a source of palladium, a species is formed which can be used to catalyse the Suzuki cross‐coupling of 4‐chloro toluene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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