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Electron‐Rich, Bicyclic Biaryl‐Like KITPHOS Monophosphines via [4+2] Cycloaddition between 1‐Alkynylphosphine Oxides and Anthracene: Highly Efficient Ligands for Palladium‐Catalysed CN and CC Bond Formation
Author(s) -
Doherty Simon,
Knight Julian G.,
Smyth Catherine H.,
Jorgenson Graeme A.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800307
Subject(s) - chemistry , cycloaddition , anthracene , bicyclic molecule , palladium , aryl , amination , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , alkyl
Electron‐rich, bicyclic biaryl‐like KITPHOS monophosphines have been prepared via Diels–Alder cycloaddition between 1‐alkynylphosphine oxides and anthracene in an operationally straightforward and highly modular synthetic protocol that will allow access to an architecturally and electronically diverse family of ligands. Palladium complexes of these ligands are highly efficient catalysts for the Buchwald–Hartwig amination and Suzuki–Miyaura coupling of a wide range of aryl chlorides, which for the vast majority of substrate combinations outperform their o ‐(dicyclohexylphosphino)biphenyl‐based counterparts.