The divergent effects of strong NHC donation in catalysis

Lummiss, Justin A. M.; Higman, Carolyn S.; Fyson, Devon L.; McDonald, Robert; Fogg, Deryn E.

doi:10.1039/c5sc02592c

Cited by 78 publications

(103 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, even with 1.25 equiv of 10 a , complex 16 a was not observed on a TLC plate even though complex 14 a was not fully consumed. This fact suggests a strong steric repulsion between CAAC and tricyclohexylphosphine in 16 a , which facilitates dissociation of the latter and complexation of the second CAAC . From practical and economical point of view, complex 14 b is the most preferred Ru source .…”

Section: Figurementioning

confidence: 99%

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Gawin¹,

Kozakiewicz

Guńka

et al. 2016

Angewandte Chemie

View full text Add to dashboard Cite

The state-of-the-art in olefin metathesis is application of N-heterocyclic carbene (NHC)-containing ruthenium alkylidenes for the formation of internal C=Cb onds and of cyclic alkyl amino carbene (CAAC)-containing ruthenium benzylidenes in the production of terminal olefins.Astraightforwards ynthesis of bis(CAAC)Ru indenylidene complexes, which are highly effective in the formation of both terminal and internal C = Cb onds at loadings as low as 1ppm, is now reported.

show abstract

Section: Figurementioning

confidence: 99%

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Gawin¹,

Kozakiewicz

Guńka

et al. 2016

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

“…This fact suggests astrong steric repulsion between CAACa nd tricyclohexylphosphine in 16 a,w hich facilitates dissociation of the latter and complexation of the second CAAC. [27] From practical and economical point of view,c omplex 14 b is the most preferred Ru source. [24] Conveniently, 15 a was obtained from 14 b as as ole product with 59 %y ield.…”

mentioning

confidence: 99%

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Gawin¹,

et al. 2016

View full text Add to dashboard Cite

The state‐of‐the‐art in olefin metathesis is application of N‐heterocyclic carbene (NHC)‐containing ruthenium alkylidenes for the formation of internal C=C bonds and of cyclic alkyl amino carbene (CAAC)‐containing ruthenium benzylidenes in the production of terminal olefins. A straightforward synthesis of bis(CAAC)Ru indenylidene complexes, which are highly effective in the formation of both terminal and internal C=C bonds at loadings as low as 1 ppm, is now reported.

show abstract

“…[5a] This procedure could help circumvent the problems associated with multistep synthesis followed by Bhaskar and Ronald in ar ecent report. [11] In recenty ears, tandemc atalytic reactions have emerged as an important tool to provide as ustainable solution for the formation of multiple CÀCo rC ÀXb onds in ao ne-pot procedure. [20] This synthetic strategy provides multiple advantages over the challengingm ultistep synthesis, such as low solvent usage,b etter yields, and the elimination of tedious isolation procedures.…”

Section: At Andem One-pot Sequential Protocol:synthesis Of Stilbene Bmentioning

confidence: 99%

“…[9,10] However, NHCs overcome the problemsa ssociated with phosphines ligand,a nd their strong sigma-electron-donating ability permits efficient activation of inert bonds. [11] NHCs have provided greater modular flexibility over steric and electronicp roperties and ease of synthesis. Because of these qualities, NHCs have been extensively exploited by many research groups, such as those of Kuhn, Hermann, Nolan, and Organ [8][9][10] One of the areas in which NHCs could play an important role is in the synthesis of stilbene-based boronate esters that have exhibited promising biological activity.…”

Section: Introductionmentioning

confidence: 99%

Novel Carbazole‐Based N‐Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd‐Catalyzed Coupling Processes

Girase

Kapdi

2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

As eries of new carbazole-based N-heterocyclic carbene (NHC)l igands have been synthesized in as imple and facile synthetic route and subsequently used in aP d/ carbazole-based NHC catalytic system, whichw as found to be effective in catalyzing Heck reactions to provide substituted stilbened erivatives in good yields. Severalb ioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a1 0mmol scale-up was also performed for trimethoxy resveratrol. The synthetic applicationw as also extended by performing ad ouble-tandem chemoselective Heck reaction followed by Miyaura borylation in ao ne-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly,aunique triple-tandemp rotocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki-Miyaura coupling reactions equence was performed for the one-pot modification of biologically relevant molecules.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Scheme2.The synthesis of novel carbazole-based NHC ligands.Scheme4.Synthesis of bioactive stilbene derivatives.Scheme5.The one-pot sequential chemoselectiveH eck/Miyaura borylation tandem protocol fort he synthesis of stilbene-basedb oronate esters.

show abstract

The divergent effects of strong NHC donation in catalysis

Abstract: The inverse relationship between NHC donicity and catalyst initiation.

Cited by 78 publications

References 53 publications

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis

Novel Carbazole‐Based N‐Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd‐Catalyzed Coupling Processes

Contact Info

Product

Resources

About