Literature DB >> 18611014

Complexes of borane and N-heterocyclic carbenes: a new class of radical hydrogen atom donor.

Shau-Hua Ueng1, Malika Makhlouf Brahmi, Etienne Derat, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Dennis P Curran.   

Abstract

Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.

Entities:  

Year:  2008        PMID： 18611014     DOI： 10.1021/ja804150k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  A Brief Survey of our Contribution to Stable Carbene Chemistry.

Authors:  David Martin; Mohand Melaimi; Michele Soleilhavoup; Guy Bertrand
Journal:  Organometallics       Date:  2011-09-22       Impact factor: 3.876

2.  Stable singlet carbenes as mimics for transition metal centers.

Authors:  David Martin; Michele Soleilhavoup; Guy Bertrand
Journal:  Chem Sci       Date:  2011-01-01       Impact factor: 9.825

3.  Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers.

Authors:  Edmund A-H Yeh; Eveline Kumli; Krishnan Damodaran; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2013-01-18       Impact factor: 15.419

4.  NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

Authors:  Laura Kuehn; Ludwig Zapf; Luis Werner; Martin Stang; Sabrina Würtemberger-Pietsch; Ivo Krummenacher; Holger Braunschweig; Emmanuel Lacôte; Todd B Marder; Udo Radius
Journal:  Chem Sci       Date:  2022-06-07       Impact factor: 9.969

5.  CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃.

Authors:  Julien Monot; Louis Fensterbank; Max Malacria; Emmanuel Lacôte; Steven J Geib; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2010-08-02       Impact factor: 2.883

6.  An overview of N-heterocyclic carbenes.

Authors:  Matthew N Hopkinson; Christian Richter; Michael Schedler; Frank Glorius
Journal:  Nature       Date:  2014-06-26       Impact factor: 49.962

7.  Efficient C-B bond formation promoted by N-heterocyclic carbenes: synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic alpha,beta-unsaturated carbonyls.

Authors:  Kang-sang Lee; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419

8.  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

9.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

10.  A radical approach for the selective C-H borylation of azines.

Authors:  Ji Hye Kim; Timothée Constantin; Marco Simonetti; Josep Llaveria; Nadeem S Sheikh; Daniele Leonori
Journal:  Nature       Date:  2021-05-20       Impact factor: 49.962
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