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BielawskiChristopher W

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N-heterocyclic carbenes: deducing sigma- and pi-contributions in Rh-catalyzed hydroboration and Pd-catalyzed coupling reactions

Author(s)
Khramov, Dimitri M.Rosen, Evelyn L.Er, Joyce An.Vu, Peter D.Lynch, Vincent M.Bielawski, Christopher W.
Issued Date
2008-07
DOI
10.1016/j.tet.2008.04.030
URI
https://scholarworks.unist.ac.kr/handle/201301/33280
Fulltext
https://www.sciencedirect.com/science/article/pii/S004040200800714X?via%3Dihub
Citation
TETRAHEDRON, v.64, no.29, pp.6853 - 6862
Abstract
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 pi-withdrawing substituents were incorporated into the NHC backbone relative to analogues bearing sigma-withdrawing groups.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
ISSN
0040-4020
Keyword
TRANSITION-METAL-COMPLEXESCHAIN ORGANOMETALLIC POLYMERSOLEFIN METATHESIS CATALYSTSSUZUKI-MIYAURAELECTRONIC-PROPERTIESARYL CHLORIDESNHC LIGANDSDEHYDROGENATIVE BORYLATION(NHC)PD(ALLYL)CL NHCSELECTIVE SYNTHESIS

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