Literature DB >> 23244023

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

Jamie M Neely1, Tomislav Rovis.   

Abstract

α,β-Unsaturated O-pivaloyl oximes are coupled to alkenes by Rh(III) catalysis to afford substituted pyridines. The reaction with activated alkenes is exceptionally regioselective and high-yielding. Mechanistic studies suggest that heterocycle formation proceeds via reversible C-H activation, alkene insertion, and a C-N bond formation/N-O bond cleavage process.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 23244023      PMCID： PMC3541442          DOI： 10.1021/ja3104389

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


  43 in total

1.  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

2.  Recent strategies for the synthesis of pyridine derivatives.

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

3.  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

4.  Rhodium catalyzed C-H olefination of N-benzoylsulfonamides with internal alkenes.

Authors:  Chen Zhu; John R Falck
Journal:  Chem Commun (Camb)       Date:  2011-12-21       Impact factor: 6.222

5.  Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates.

Authors:  Tian-Jun Gong; Bin Xiao; Zhao-Jing Liu; Jian Wan; Jun Xu; Dong-Fen Luo; Yao Fu; Lei Liu
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

6.  Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives.

Authors:  Chao Feng; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2011-08-18       Impact factor: 6.222

7.  Rollover cyclometalation pathway in rhodium catalysis: dramatic NHC effects in the C-H bond functionalization.

Authors:  Jaesung Kwak; Youhwa Ohk; Yousung Jung; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2012-10-09       Impact factor: 15.419

8.  Rhodium-catalyzed mono- and divinylation of 1-phenylpyrazoles and related compounds via regioselective C-H bond cleavage.

Authors:  Nobuyoshi Umeda; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

9.  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

10.  A simple, modular synthesis of substituted pyridines.

Authors:  Songbai Liu; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2008-05-09       Impact factor: 15.419
View more
  24 in total

1.  Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-07-20       Impact factor: 6.005

2.  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

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.  Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Authors:  Yajing Lian; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

6.  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation.

Authors:  Fedor Romanov-Michailidis; Kassandra F Sedillo; Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-07-08       Impact factor: 15.419

7.  Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

Authors:  Adam B Weinstein; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

8.  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

9.  Functionalization of C-H bonds in acetophenone oximes with arylacetic acids and elemental sulfur.

Authors:  Phuc H Pham; Khang X Nguyen; Hoai T B Pham; Thien T Tran; Tung T Nguyen; Nam T S Phan
Journal:  RSC Adv       Date:  2020-03-17       Impact factor: 4.036

10.  Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.

Authors:  Yajing Lian; Robert G Bergman; Luke D Lavis; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-05-03       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.