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Literature DB >> 21082771

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes.

Pei Chui Too¹, Yi-Feng Wang, Shunsuke Chiba.

Abstract

A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl(2)](2)-NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C-H vinylation via ortho-rhodation and C-N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

Entities: Chemical

Year: 2010 PMID： 21082771 DOI： 10.1021/ol102504b

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

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Cited

16 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. 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

Review 3. 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

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. Rh^I/Rh^III 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

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes.

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

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

Review 3. Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

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

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

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

7. Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles.

8. Unified synthesis of mono/bis-arylated phenols via Rh^III-catalyzed dehydrogenative coupling.

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

10. Rh^I/Rh^III catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.