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Literature DB >> 19067651

Versatile Pd(II)-catalyzed C-H activation/aryl-aryl coupling of benzoic and phenyl acetic acids.

Dong-Hui Wang¹, Tian-Sheng Mei, Jin-Quan Yu.

Abstract

The use of aryltrifluoroborates as coupling partners and O(2) as the oxidant substantially improves the scope and practicality of the Pd-catalyzed C-H activation/C-C coupling reaction. The newly discovered protocol made possible, for the first time, the ortho-coupling of electron-deficient arenes and phenyl acetic acids with organometallic reagents.

Entities: Chemical Disease Gene

Mesh：

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Year: 2008 PMID： 19067651 PMCID： PMC2630538 DOI： 10.1021/ja806681z

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

16 in total

1. Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter.

Authors: Xiao Chen; Jiao-Jie Li; Xue-Shi Hao; Charles E Goodhue; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2006-01-11 Impact factor: 15.419

2. Anilide ortho-arylation by using C-H activation methodology.

Authors: Olafs Daugulis; Vladimir G Zaitsev
Journal: Angew Chem Int Ed Engl Date: 2005-06-27 Impact factor: 15.336

3. Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis.

Authors: Keith M Gligorich; Matthew S Sigman
Journal: Angew Chem Int Ed Engl Date: 2006-10-13 Impact factor: 15.336

Review 4. Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors: Sylvain Darses; Jean-Pierre Genet
Journal: Chem Rev Date: 2007-12-21 Impact factor: 60.622

5. Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization.

Authors: Shangdong Yang; Bijie Li; Xiaobing Wan; Zhangjie Shi
Journal: J Am Chem Soc Date: 2007-04-25 Impact factor: 15.419

Review 6. Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer--a biomimetic approach.

Authors: Julio Piera; Jan-E Bäckvall
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

8. Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: two distinct C-H activation pathways.

Authors: Xiao Chen; Charles E Goodhue; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2006-10-04 Impact factor: 15.419

9. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors: Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal: J Am Chem Soc Date: 2005-05-25 Impact factor: 15.419

Review 10. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors: Shannon S Stahl
Journal: Angew Chem Int Ed Engl Date: 2004-06-28 Impact factor: 15.336

37 in total

1. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

Authors: Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

10. The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors: Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal: Adv Synth Catal Date: 2011-05-01 Impact factor: 5.837

Versatile Pd(II)-catalyzed C-H activation/aryl-aryl coupling of benzoic and phenyl acetic acids.

1. Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter.

2. Anilide ortho-arylation by using C-H activation methodology.

3. Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis.

Review 4. Potassium organotrifluoroborates: new perspectives in organic synthesis.

5. Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization.

Review 6. Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer--a biomimetic approach.

7. Palladium-catalyzed cross-coupling reactions in total synthesis.

8. Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: two distinct C-H activation pathways.

9. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Review 10. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

1. Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a Mn^III Oxidant under Mild Conditions.

2. Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands.

3. Innate and guided C-H functionalization logic.

4. A general method for copper-catalyzed arene cross-dimerization.

5. Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Review 6. A Simple and Versatile Amide Directing Group for C-H Functionalizations.

7. Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

8. Ligand-enabled reactivity and selectivity in a synthetically versatile aryl C-H olefination.

9. Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

10. The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.