Literature DB >> 22332639

Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization.

Rhia M Martin1, Robert G Bergman, Jonathan A Ellman.   

Abstract

An expedient one-pot rhodium catalyzed C-H bond functionalization/electrocyclization/dehydration procedure has been developed for the synthesis of highly substituted pyridine derivatives from terminal alkynes and α,β-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.

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Year:  2012        PMID： 22332639      PMCID： PMC3292635          DOI： 10.1021/jo202280e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  20 in total

1.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors:  Jesús A Varela; Carlos Saá
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

3.  Direct synthesis of pyridine derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill; Omar K Ahmad
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

4.  Intermolecular cope-type hydroamination of alkenes and alkynes.

Authors:  André M Beauchemin; Joseph Moran; Marie-Eve Lebrun; Catherine Séguin; Elena Dimitrijevic; Lili Zhang; Serge I Gorelsky
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Efficient and stereoselective access to the polyol fragment C9-C16 of ansamycin antibiotics.

Authors:  Michel Obringer; Marie Barbarotto; Sabine Choppin; Françoise Colobert
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

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

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-10       Impact factor: 6.222

7.  A convenient rhodium-catalyzed intermolecular hydroamination procedure for terminal alkynes.

Authors:  C G Hartung; A Tillack; H Trauthwein; M Beller
Journal:  J Org Chem       Date:  2001-09-21       Impact factor: 4.354

8.  Selective preparation of pyridines, pyridones, and iminopyridines from two different alkynes via azazirconacycles.

Authors:  Tamotsu Takahashi; Fu-Yu Tsai; Yanzhong Li; Hui Wang; Yoshihiko Kondo; Masamichi Yamanaka; Kiyohiko Nakajima; Martin Kotora
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

9.  Dimerization of terminal alkynes catalyzed by a nickel complex having a bulky phosphine ligand.

Authors:  Sensuke Ogoshi; Mizu Ueta; Masa-aki Oka; Hideo Kurosawa
Journal:  Chem Commun (Camb)       Date:  2004-10-08       Impact factor: 6.222

10.  Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.

Authors:  Barry M Trost; Alicia C Gutierrez
Journal:  Org Lett       Date:  2007-03-16       Impact factor: 6.005
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  11 in total

1.  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

2.  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

3.  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

4.  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

5.  Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

Authors:  Michael A Ischay; Michael K Takase; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-02-11       Impact factor: 15.419

6.  Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.

Authors:  Yuji Matsushima; Eric M Phillips; Robert G Bergman; Jonathan A Ellman
Journal:  Synlett       Date:  2015-02-27       Impact factor: 2.454

Review 7.  Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.

Authors:  Sun Dongbang; Danielle N Confair; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2021-03-19       Impact factor: 22.384

8.  Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-02-10       Impact factor: 15.419

Review 9.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317

10.  Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

Authors:  Dimitra Kontokosta; Daniel S Mueller; Dong-Liang Mo; Wiktoria H Pace; Rachel A Simpson; Laura L Anderson
Journal:  Beilstein J Org Chem       Date:  2015-11-04       Impact factor: 2.883
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