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Literature DB >> 31021606

Palladium/Norbornene Cooperative Catalysis.

Abstract

Palladium/norbornene cooperative catalysis has emerged as a distinct approach to construct polyfunctionalized arenes from readily available starting materials. This Review provides a comprehensive overview of this field, including the early stoichiometric investigations, catalytic reaction developments, as well as the applications in the syntheses of bioactive compounds and polymers. The section of catalytic reactions is divided into two parts according to the reaction initiation mode: Pd(0)-initiated reactions and Pd(II)-initiated reactions.

Entities: Chemical Disease Species

Year: 2019 PMID： 31021606 PMCID： PMC7075350 DOI： 10.1021/acs.chemrev.9b00079

Source DB: PubMed Journal: Chem Rev ISSN： 0009-2665 Impact factor: 60.622

179 in total

1. Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction.

Authors: Koichi Mitsudo; Praew Thansandote; Thorsten Wilhelm; Brian Mariampillai; Mark Lautens
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

2. Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[ d]oxazoles.

Authors: Pingshun Zhang; Shanfei Pan; Wanzhi Chen; Miaochang Liu; Huayue Wu
Journal: J Org Chem Date: 2018-02-26 Impact factor: 4.354

3. Synthesis of pyrrolophenanthridine alkaloids based on C(sp³)-H and C(sp²)-H functionalization reactions.

Authors: Chihiro Tsukano; Nobusuke Muto; Iderbat Enkhtaivan; Yoshiji Takemoto
Journal: Chem Asian J Date: 2014-07-14

4. 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

5. Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction.

Authors: Harish Kumar Potukuchi; Thorsten Bach
Journal: J Org Chem Date: 2013-11-15 Impact factor: 4.354

6. Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: mechanism and applications.

Authors: Lei Jiao; Eberhardt Herdtweck; Thorsten Bach
Journal: J Am Chem Soc Date: 2012-08-22 Impact factor: 15.419

7. Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles.

Authors: Alena Rudolph; Nils Rackelmann; Marc-Olivier Turcotte-Savard; Mark Lautens
Journal: J Org Chem Date: 2009-01-02 Impact factor: 4.354

8. Meta-Selective C-H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

Authors: Qiankun Li; Eric M Ferreira
Journal: Chemistry Date: 2017-08-07 Impact factor: 5.236

9. Synthesis of Benzo[1,6]naphthyridinones Using the Catellani Reaction.

Authors: Mohamed S A Elsayed; Brittany Griggs; Mark Cushman
Journal: Org Lett Date: 2018-08-13 Impact factor: 6.005

10. Total synthesis of (+)-linoxepin by utilizing the Catellani reaction.

Authors: Harald Weinstabl; Marcel Suhartono; Zafar Qureshi; Mark Lautens
Journal: Angew Chem Int Ed Engl Date: 2013-04-16 Impact factor: 15.336

26 in total

1. Cobalt(III)-Catalyzed Diastereoselective Three-Component C-H Bond Addition to Butadiene and Activated Ketones.

Authors: Zican Shen; Chen Li; Brandon Q Mercado; Jonathan A Ellman
Journal: Synthesis (Stuttg) Date: 2019-11-07 Impact factor: 3.157

2. Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis.

Authors: Zhao Wu; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2022-03-04 Impact factor: 15.336

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

4. Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.

Authors: Renhe Li; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2021-11-10 Impact factor: 15.336

5. Compatibility Score for Rational Electrophile Selection in Pd/NBE Cooperative Catalysis.

Authors: Xiaotian Qi; Jianchun Wang; Zhe Dong; Guangbin Dong; Peng Liu
Journal: Chem Date: 2020-10-01 Impact factor: 22.804

Review 6. Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors: Renhe Li; Guangbin Dong
Journal: J Am Chem Soc Date: 2020-10-05 Impact factor: 15.419

10. Modular Entry to Functionalized Tetrahydrobenzo[b]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene.

Authors: Xin Liu; Jianchun Wang; Guangbin Dong
Journal: J Am Chem Soc Date: 2021-06-23 Impact factor: 16.383

Palladium/Norbornene Cooperative Catalysis.

1. Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction.

2. Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[ d]oxazoles.

3. Synthesis of pyrrolophenanthridine alkaloids based on C(sp³)-H and C(sp²)-H functionalization reactions.

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

5. Selective C-2 alkylation of tryptophan by a Pd(II)/norbornene-promoted C-H activation reaction.

6. Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: mechanism and applications.

7. Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles.

8. Meta-Selective C-H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

9. Synthesis of Benzo[1,6]naphthyridinones Using the Catellani Reaction.

10. Total synthesis of (+)-linoxepin by utilizing the Catellani reaction.

1. Cobalt(III)-Catalyzed Diastereoselective Three-Component C-H Bond Addition to Butadiene and Activated Ketones.

2. Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

4. Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.

5. Compatibility Score for Rational Electrophile Selection in Pd/NBE Cooperative Catalysis.

Review 6. Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

7. Unexpected ortho-Heck Reaction under the Catellani Conditions.

8. Diversity-oriented functionalization of 2-pyridones and uracils.

9. Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

10. Modular Entry to Functionalized Tetrahydrobenzo[b]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 6. Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.