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Pd‐PEPPSI‐IPent: An Active, Sterically Demanding Cross‐Coupling Catalyst and Its Application in the Synthesis of Tetra‐ Ortho ‐Substituted Biaryls
Author(s) -
Organ Michael G.,
Çalimsiz Selçuk,
Sayah Mahmoud,
Hoi Ka Hou,
Lough Alan J.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805661
Subject(s) - steric effects , carbene , catalysis , tetra , aryl , chemistry , coupling reaction , polymer chemistry , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl
Incredible Bulk : A series of N‐heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki–Miyaura reaction. A variety of sterically encumbered tetra‐ ortho ‐substituted biaryl products were formed from unreactive aryl chlorides using the isopentyl‐substituted catalyst at temperatures ranging from 65 °C to room temperature. The cyclopentyl‐substituted catalyst was virtually inactive, demonstrating that “flexible bulk” is essential to promote these transformations.