Surveying sterically demanding N-heterocyclic carbene ligands with restricted flexibility for palladium-catalyzed cross-coupling reactions

Accounts of Chemical Research
Sebastian Würtz, Frank Glorius

Abstract

Heterocyclic carbenes (NHCs), especially monodentate ones, have become the ligand of choice for many transition-metal-catalyzed transformations. They generally form highly stable complexes, have strong sigma-donor character, and have a unique shape that can be used to generate sterically demanding ligands.In this Account, we survey recent developments in the design and synthesis of some sterically demanding NHCs with a particularly strong influence on the metal's coordination sphere. We show the successful and insightful application of these ligands in transition-metal catalysis. First, we discuss methods for determining and classifying the electronic and steric properties of NHCs. In addition, we present data on the most important NHC ligands.The selective variation of either electronic or steric parameters of NHCs, and therefore of the catalyst, allows for the optimization of the reaction. Thus, we prepared several series of differentially substituted NHC derivatives. However, because the substituents varied were not directly connected to the carbene carbon, it was difficult to induce a large electronic variation. In contrast, an independent variation of the ligands' steric properties was more straightforward. We highlight th...Continue Reading

References

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Citations

Jul 15, 2011·Accounts of Chemical Research·Akkattu T BijuFrank Glorius
Jan 18, 2011·Chemical Reviews·Laure BenhamouVincent César
Oct 15, 2009·Chemical Communications : Chem Comm·Tieqiang ZengChao-Jun Li
Jan 29, 2010·Chemical Communications : Chem Comm·Hervé Clavier, Steven P Nolan
May 21, 2010·Chemical Communications : Chem Comm·Dehui WangChunying Duan
Jun 10, 2010·Chemical Communications : Chem Comm·Kyle A Williams, Christopher W Bielawski
Mar 19, 2011·Chemical Communications : Chem Comm·Marcus RoseStefan Kaskel
Sep 2, 2011·Chemical Communications : Chem Comm·Richard A LayfieldFloriana Tuna
Jan 14, 2012·Chemical Communications : Chem Comm·Günter Seidel, Alois Fürstner
Jan 13, 2012·Chemical Communications : Chem Comm·Shabana KhanHerbert W Roesky
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Jin-Tao GuanSi-Yin Zhao
Oct 21, 2015·Chemistry : a European Journal·Luis Miguel Martínez-PrietoBruno Chaudret
Mar 5, 2016·Chemical Communications : Chem Comm·L M Martínez-PrietoF Glorius
Aug 13, 2009·Angewandte Chemie·Julia J NeumannFrank Glorius
Mar 27, 2009·Angewandte Chemie·Guillaume Berthon-GellozIstván E Markó
Oct 29, 2010·Chemistry : a European Journal·Matthew G HobbsRoland Roesler
Jul 29, 2011·Chemistry : a European Journal·Qiwu ZhaoEmmanuel Lacôte
Nov 29, 2011·Chemistry : a European Journal·Philippe RibagnacNicolas Mézailles
Mar 13, 2012·Angewandte Chemie·Orestes Rivada-WheelaghanSalvador Conejero
Oct 12, 2013·Chemistry : a European Journal·Laura Rubio-PérezLuis A Oro
May 23, 2012·Chemistry : a European Journal·Isabel MeanaPablo Espinet
Jan 13, 2011·Chemistry : a European Journal·Kun HuangZhang-Jie Shi
Feb 9, 2012·Angewandte Chemie·Nuria OrtegaFrank Glorius
Sep 14, 2010·Angewandte Chemie·Mohand MelaimiGuy Bertrand
Aug 18, 2010·Angewandte Chemie·Thomas Dröge, Frank Glorius
Jul 13, 2012·Chemistry : a European Journal·Rylan J Lundgren, Mark Stradiotto
Sep 8, 2010·Chemistry : a European Journal·Vincent CésarGuy Lavigne
Apr 16, 2011·Angewandte Chemie·Isabel PielFrank Glorius
Apr 28, 2011·Angewandte Chemie·Lan-Gui Xie, Zhong-Xia Wang
Sep 17, 2010·Angewandte Chemie·Kalluri V S RanganathFrank Glorius

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