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Literature DB >> 19296661

Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.

Yang-Hui Zhang¹, Bing-Feng Shi, Jin-Quan Yu.

Abstract

Pd(II)-catalyzed meta-olefination of highly electron-deficient arenes is achieved through the use of a rationally designed mutually repulsive ligand. The combination of directed and nondirected C-H functionalization of arenes provides a versatile route for the synthesis of highly sought after 1,2,4-trisubstituted arenes.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2009 PMID： 19296661 PMCID： PMC2667208 DOI： 10.1021/ja900327e

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

26 in total

1. 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

2. 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

3. Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by Pd(II)-catalyzed C-H activation reactions.

Authors: Jiao-Jie Li; Tian-Sheng Mei; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Pd nanoparticles catalyzed stereospecific synthesis of beta-aryl cinnamic esters in ionic liquids.

Authors: Vincenzo Caló; Angelo Nacci; Antonio Monopoli; Stefania Laera; Nicola Cioffi
Journal: J Org Chem Date: 2003-04-04 Impact factor: 4.354

5. Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

Authors: Maarten D K Boele; Gino P F van Strijdonck; André H M de Vries; Paul C J Kamer; Johannes G de Vries; Piet W N M van Leeuwen
Journal: J Am Chem Soc Date: 2002-02-27 Impact factor: 15.419

6. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors: Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

7. A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Authors: Phil S Baran; E J Corey
Journal: J Am Chem Soc Date: 2002-07-10 Impact factor: 15.419

Review 8. 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

9. Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

Authors: Chris E Houlden; Chris D Bailey; J Gair Ford; Michel R Gagné; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal: J Am Chem Soc Date: 2008-07-10 Impact factor: 15.419

10. Direct coupling of benzene with olefin catalyzed by Pd(OAc)(2) combined with heteropolyoxometalate under dioxygen.

Authors: Takahiro Yokota; Masayuki Tani; Satoshi Sakaguchi; Yasutaka Ishii
Journal: J Am Chem Soc Date: 2003-02-12 Impact factor: 15.419

59 in total

1. Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors: Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal: J Am Chem Soc Date: 2010-11-03 Impact factor: 15.419

Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.

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

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

3. Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by Pd(II)-catalyzed C-H activation reactions.

4. Pd nanoparticles catalyzed stereospecific synthesis of beta-aryl cinnamic esters in ionic liquids.

5. Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

6. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

7. A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Review 8. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

9. Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

10. Direct coupling of benzene with olefin catalyzed by Pd(OAc)(2) combined with heteropolyoxometalate under dioxygen.

1. Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

2. Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

3. A meta-selective C-H borylation directed by a secondary interaction between ligand and substrate.

4. Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

5. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

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

7. Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

8. Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

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

10. Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives.