Literature DB >> 20377234

Rhodium-catalyzed oxidative coupling/cyclization of 2-phenylindoles with alkynes via C-H and N-H bond cleavages with air as the oxidant.

Keisuke Morimoto1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

The straightforward and efficient synthesis of indolo[2,1-a]isoquinoline derivatives has been achieved by the rhodium-catalyzed aerobic oxidative coupling/cyclization of 2-phenylindoles with alkynes. Some of the polycyclic products exhibit solid-state fluorescence.

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Year:  2010        PMID： 20377234     DOI： 10.1021/ol100560k

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


  16 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

2.  Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles.

Authors:  Gia L Hoang; Jonathan A Ellman
Journal:  Tetrahedron       Date:  2018-03-31       Impact factor: 2.457

3.  Synthesis of [5,6]-Bicyclic Heterocycles with a Ring-Junction Nitrogen Atom: Rhodium(III)-Catalyzed C-H Functionalization of Alkenyl Azoles.

Authors:  Kim Søholm Halskov; Howard S Roth; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-05       Impact factor: 15.336

4.  Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

5.  Visible-light-promoted decarboxylative radical cascade cyclization to acylated benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones in water.

Authors:  Lili Tang; Yuejun Ouyang; Kai Sun; Bing Yu
Journal:  RSC Adv       Date:  2022-07-07       Impact factor: 4.036

6.  Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Melissa A Ashley; Maria Romanova-Michaelides; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

7.  Rhodium(III)-Catalyzed Imidoyl C-H Activation for Annulations to Azolopyrimidines.

Authors:  Kim Søholm Halskov; Michael R Witten; Gia L Hoang; Brandon Q Mercado; Jonathan A Ellman
Journal:  Org Lett       Date:  2018-03-27       Impact factor: 6.005

8.  Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams.

Authors:  Shangze Wu; Rong Zeng; Chunling Fu; Yihua Yu; Xue Zhang; Shengming Ma
Journal:  Chem Sci       Date:  2015-02-05       Impact factor: 9.825

9.  Rh(III)-catalyzed cyclopropanation initiated by C-H activation: ligand development enables a diastereoselective [2 + 1] annulation of N-enoxyphthalimides and alkenes.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-08-05       Impact factor: 15.419

10.  RhI/RhIII catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.

Authors:  Ángel Manu Martínez; Javier Echavarren; Inés Alonso; Nuria Rodríguez; Ramón Gómez Arrayás; Juan C Carretero
Journal:  Chem Sci       Date:  2015-06-29       Impact factor: 9.825
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