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Literature DB >> 21913636

Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Keary M Engle¹, Peter S Thuy-Boun, Michael Dang, Jin-Quan Yu.

Abstract

A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag(2)CO(3) as the oxidant, a fast, high-yielding, operationally simple, and functional group-tolerant protocol has been developed for the cross-coupling of phenylacetic acid substrates with aryltrifluoroborates. This ligand scaffold has also been shown to improve catalysis using 1 atm O(2) as the sole reoxidant, which sheds light on the path forward in developing optimized ligands for aerobic C-H/arylboron cross-coupling.

Entities: Chemical Disease Gene

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Year: 2011 PMID： 21913636 PMCID： PMC3230269 DOI： 10.1021/ja203978r

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

97 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. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors: Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal: Isr J Chem Date: 2010-12 Impact factor: 3.333

3. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

Authors: Fumitoshi Kakiuchi; Shintaro Kan; Kimitaka Igi; Naoto Chatani; Shinji Murai
Journal: J Am Chem Soc Date: 2003-02-19 Impact factor: 15.419

4. Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

Authors: Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

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. 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

7. Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination.

Authors: Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2010-08-16 Impact factor: 15.336

8. Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd(II)-2,6-pyridinedicarboxylic acid systems.

Authors: Jing Zhang; Eugene Khaskin; Nicholas P Anderson; Peter Y Zavalij; Andrei N Vedernikov
Journal: Chem Commun (Camb) Date: 2008-06-16 Impact factor: 6.222

Review 9. 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

10. Two methods for direct ortho-arylation of benzoic acids.

Authors: Hendrich A Chiong; Quynh-Nhu Pham; Olafs Daugulis
Journal: J Am Chem Soc Date: 2007-07-25 Impact factor: 15.419

23 in total

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors: Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal: Organic Synth Date: 2015-03-12

2. 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

Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

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

2. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

3. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

4. Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

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

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

7. Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination.

8. Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd(II)-2,6-pyridinedicarboxylic acid systems.

Review 9. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

10. Two methods for direct ortho-arylation of benzoic acids.

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

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

3. Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

4. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

5. Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst.

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

Review 7. Enantioselective C(sp³)‒H bond activation by chiral transition metal catalysts.

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

9. Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3.

10. Catalytic Behavior of Mono-N-Protected Amino-Acid Ligands in Ligand-Accelerated C-H Activation by Palladium(II).

Review 9. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Review 7. Enantioselective C(sp3)‒H bond activation by chiral transition metal catalysts.

Review 7. Enantioselective C(sp³)‒H bond activation by chiral transition metal catalysts.