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Literature DB >> 22149270

N-Heterocyclic carbene boranes are good hydride donors.

Markus Horn¹, Herbert Mayr, Emmanuel Lacôte, Everett Merling, Jordan Deaner, Sarah Wells, Timothy McFadden, Dennis P Curran.

Abstract

The nucleophilicity parameters (N) of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane and 1,3-dimethylimidazol-2-ylidene borane are 9.55 and 11.88. This places N-heterocyclic carbene boranes (NHC-boranes) among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C═N and C═C bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants.

Entities: Chemical Disease

Year: 2011 PMID： 22149270 DOI： 10.1021/ol202836p

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.

Authors: Aleksandrs Prokofjevs; Anne Boussonnière; Linfeng Li; Hélène Bonin; Emmanuel Lacôte; Dennis P Curran; Edwin Vedejs
Journal: J Am Chem Soc Date: 2012-07-16 Impact factor: 15.419

2. Influence of Electronic Effects on the Reactivity of Triazolylidene-Boryl Radicals: Consequences for the use of N-Heterocyclic Carbene Boranes in Organic and Polymer Synthesis.

Authors: Sofia Telitel; Anne-Laure Vallet; Darrin M Flanigan; Bernadette Graff; Fabrice Morlet-Savary; Tomislav Rovis; Jacques Lalevée; Emmanuel Lacôte
Journal: Chemistry Date: 2015-08-03 Impact factor: 5.236

7. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.

Authors: James E Radcliffe; Valerio Fasano; Ralph W Adams; Peiran You; Michael J Ingleson
Journal: Chem Sci Date: 2018-11-19 Impact factor: 9.825

7 in total

N-Heterocyclic carbene boranes are good hydride donors.

1. Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.

2. Influence of Electronic Effects on the Reactivity of Triazolylidene-Boryl Radicals: Consequences for the use of N-Heterocyclic Carbene Boranes in Organic and Polymer Synthesis.

3. A quantitative approach to nucleophilic organocatalysis.

Review 4. Radicals: Reactive Intermediates with Translational Potential.

5. Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid.

6. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

7. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.

N-Heterocyclic carbene boranes are good hydride donors.

1. Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.

2. Influence of Electronic Effects on the Reactivity of Triazolylidene-Boryl Radicals: Consequences for the use of N-Heterocyclic Carbene Boranes in Organic and Polymer Synthesis.

3. A quantitative approach to nucleophilic organocatalysis.

Review 4. Radicals: Reactive Intermediates with Translational Potential.

5. Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid.

6. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

7. Reductive α-borylation of α,β-unsaturated esters using NHC-BH3 activated by I2 as a metal-free route to α-boryl esters.

7. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.