N-Heterocyclic carbenes: deducing σ- and π-contributions in Rh-catalyzed hydroboration and Pd-catalyzed coupling reactions

Autor:	Joyce A.V. Er, Dimitri M. Khramov, Peter D. Vu, Vincent M. Lynch, Christopher W. Bielawski, Evelyn L. Rosen
Rok vydání:	2008
Předmět:	Hydroboration chemistry.chemical_compound Tolman electronic parameter Chemistry Organic Chemistry Drug Discovery Organic chemistry Biochemistry Medicinal chemistry Carbene Coupling reaction Catalysis Electronic properties
Zdroj:	Tetrahedron. 64:6853-6862
ISSN:	0040-4020
DOI:	10.1016/j.tet.2008.04.030
Popis:	The effect of tuning the electronic properties of N-heterocyclic carbene (NHC) ligands was evaluated in multiple, mechanistically distinct, metal-mediated reactions. Hydroboration and Heck reactions, catalyzed by Rh–NHC and Pd–NHC complexes, respectively, were found to result in yields that were up to ten times lower when π-withdrawing substituents were incorporated into the NHC backbone relative to analogues bearing σ-withdrawing groups.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e05e65b6ee44b9e7883fed18c6b517f7 https://doi.org/10.1016/j.tet.2008.04.030 Zobrazit plný text záznamu Full Text from ScienceDirect