Literature DB >> 21986995

Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Todd K Hyster1, Tomislav Rovis.   

Abstract

The synthesis of pyridines from readily available α,β-unsaturated oximes and alkynes under mild conditions and low temperatures using Rh(III) catalysis has been developed. It was found that the use of sterically different ligands allows for complementary selectivities to be achieved. This journal is © The Royal Society of Chemistry 2011

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Year:  2011        PMID： 21986995      PMCID： PMC3430144          DOI： 10.1039/c1cc15248c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  51 in total

1.  Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides.

Authors:  Guoyong Song; Dan Chen; Cheng-Ling Pan; Robert H Crabtree; Xingwei Li
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

2.  Recent strategies for the synthesis of pyridine derivatives.

Authors:  Matthew D Hill
Journal:  Chemistry       Date:  2010-10-25       Impact factor: 5.236

3.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

Review 4.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

5.  Rh(III)-catalyzed oxidative olefination of vinylic C-H bonds: efficient and selective access to di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes.

Authors:  Tatiana Besset; Nadine Kuhl; Frederic W Patureau; Frank Glorius
Journal:  Chemistry       Date:  2011-05-25       Impact factor: 5.236

6.  Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors:  Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

7.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles.

Authors:  David R Stuart; Pamela Alsabeh; Michelle Kuhn; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2010-12-06       Impact factor: 15.419

8.  Iron-catalyzed cycloaddition of alkynenitriles and alkynes.

Authors:  Brendan R D'Souza; Timothy K Lane; Janis Louie
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

9.  The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles.

Authors:  Malcolm P Huestis; Lina Chan; David R Stuart; Keith Fagnou
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

10.  One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles.

Authors:  James R Manning; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419
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  33 in total

1.  Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Maria Romanova-Michaelides; Kelvin E Jackson; Natthawat Semakul; Trevor D Taggart; Brian S Newell; Christopher D Rithner; Robert S Paton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-01-06       Impact factor: 15.419

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

3.  Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines.

Authors:  Shuming Chen; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2015-05-20       Impact factor: 6.005

Review 4.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

5.  Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

Authors:  Yajing Lian; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Sci       Date:  2012-08-02       Impact factor: 9.825

6.  A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.

Authors:  Todd K Hyster; Kyle E Ruhl; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-04-02       Impact factor: 15.419

7.  Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Authors:  Alexis Archambeau; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-11       Impact factor: 15.336

8.  Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2013-01-15       Impact factor: 6.005

9.  Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-12-18       Impact factor: 15.419

10.  The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors:  Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222
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