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Literature DB >> 23002028

Access to sultams by rhodium(III)-catalyzed directed C-H activation.

Manh V Pham¹, Baihua Ye, Nicolai Cramer.

Abstract

Director's cut: The pharmaceutically relevant sulfonamide group is shown to be a competent directing group for [Cp*Rh(OAc)(2)]-catalyzed C-H functionalizations. Reactions of the cyclometalated intermediate with internal alkynes provide access to a wide range of sultam derivatives. The reaction is high yielding and works best under aerobic conditions with catalytic amounts of CuOAc as an oxidation mediator. Cp* = C(5)Me(5).

Entities: Chemical

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Year: 2012 PMID： 23002028 DOI： 10.1002/anie.201206191

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

15 in total

1. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

Authors: Joanna Wencel-Delord; Frank Glorius
Journal: Nat Chem Date: 2013-05 Impact factor: 24.427

2. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

Authors: Daniel R Wallach; John D Chisholm
Journal: J Org Chem Date: 2016-08-10 Impact factor: 4.354

3. meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

Authors: Guolin Cheng; Peng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-06-09 Impact factor: 15.336

4. Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors: Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: Org Lett Date: 2013-03-15 Impact factor: 6.005

Review 5. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors: Keary M Engle; Jin-Quan Yu
Journal: J Org Chem Date: 2013-05-03 Impact factor: 4.354

Access to sultams by rhodium(III)-catalyzed directed C-H activation.

1. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

2. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

3. meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

4. Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Review 5. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

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

7. Merging rhodium-catalysed C-H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation.

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

9. A C-H bond activation-based catalytic approach to tetrasubstituted chiral allenes.

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