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Literature DB >> 22500854

Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Kevin D Hesp¹, Robert G Bergman, Jonathan A Ellman.

Abstract

Rhodium-catalyzed addition of n class="Chemical">benzamide C-H bonds to a range of aromatic N-sulfonyl aldimines has been developed and proceeds with high functional group compatibility. The synthetic utility of the resulting branched amine products has also been demonstrated by the preparation of isoindoline and isoindolinone frameworks.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2012 PMID： 22500854 PMCID： PMC3345069 DOI： 10.1021/ol300723x

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

25 in total

1. Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

Authors: Ya Du; Todd K Hyster; Tomislav Rovis
Journal: Chem Commun (Camb) Date: 2011-10-17 Impact factor: 6.222

2. Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors: Tetsuya Satoh; Masahiro Miura
Journal: Chemistry Date: 2010-10-04 Impact factor: 5.236

Review 3. Towards mild metal-catalyzed C-H bond activation.

Authors: Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal: Chem Soc Rev Date: 2011-06-10 Impact factor: 54.564

4. Rhodium-catalyzed direct addition of aryl C-H bonds to N-sulfonyl aldimines.

Authors: Yang Li; Bi-Jie Li; Wen-Hua Wang; Wei-Ping Huang; Xi-Sha Zhang; Kang Chen; Zhang-Jie Shi
Journal: Angew Chem Int Ed Engl Date: 2011-01-26 Impact factor: 15.336

5. Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Authors: Andy S Tsai; Michael E Tauchert; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2011-01-04 Impact factor: 15.419

6. Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

Authors: Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2011-07-08 Impact factor: 15.419

7. Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes: direct functionalization of the sp2 C-H bond.

Authors: Jihye Park; Eonjeong Park; Aejin Kim; Youngil Lee; Ki-Whan Chi; Jong Hwan Kwak; Young Hoon Jung; In Su Kim
Journal: Org Lett Date: 2011-07-27 Impact factor: 6.005

8. Ns strategies: a highly versatile synthetic method for amines.

Authors: Toshiyuki Kan; Tohru Fukuyama
Journal: Chem Commun (Camb) Date: 2003-11-25 Impact factor: 6.222

Review 9. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

10. Synthesis of aryl ketones by the PD-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles.

Authors: Chengxiang Zhou; Richard C Larock
Journal: J Am Chem Soc Date: 2004-03-03 Impact factor: 15.419

16 in total

1. Combined electrochemical/chemical methods for the synthesis and the molecular diversifying of isoindolinone-based heterocyclic scaffolds.

Authors: Laura Palombi; Antonia Di Mola; Chiara Vignes; Antonio Massa
Journal: Mol Divers Date: 2014-01-12 Impact factor: 2.943

Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

1. Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

2. Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Review 3. Towards mild metal-catalyzed C-H bond activation.

4. Rhodium-catalyzed direct addition of aryl C-H bonds to N-sulfonyl aldimines.

5. Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

6. Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

7. Rhodium-catalyzed oxidative ortho-acylation of benzamides with aldehydes: direct functionalization of the sp2 C-H bond.

8. Ns strategies: a highly versatile synthetic method for amines.

Review 9. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

10. Synthesis of aryl ketones by the PD-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles.

1. Combined electrochemical/chemical methods for the synthesis and the molecular diversifying of isoindolinone-based heterocyclic scaffolds.

2. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

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

4. Cobalt(III)-Catalyzed C-H Bond Amidation with Isocyanates.

5. Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

6. Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

7. An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation.

8. Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes.

9. Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

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