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Literature DB >> 28391681

Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp³)-H Bonds.

Ru-Yi Zhu¹, Tyler G Saint-Denis¹, Ying Shao¹, Jian He¹, Joshua D Sieber², Chris H Senanayake², Jin-Quan Yu¹.

Abstract

We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands.

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Year: 2017 PMID： 28391681 PMCID： PMC5535776 DOI： 10.1021/jacs.7b02196

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

34 in total

1. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors: Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2005-03-29 Impact factor: 15.336

Review 2. Nature's inventory of halogenation catalysts: oxidative strategies predominate.

Authors: Frédéric H Vaillancourt; Ellen Yeh; David A Vosburg; Sylvie Garneau-Tsodikova; Christopher T Walsh
Journal: Chem Rev Date: 2006-08 Impact factor: 60.622

3. Sulfoximine assisted Pd(II)-catalyzed bromination and chlorination of primary β-C(sp3)-H bond.

Authors: Raja K Rit; M Ramu Yadav; Koushik Ghosh; Majji Shankar; Akhila K Sahoo
Journal: Org Lett Date: 2014-09-30 Impact factor: 6.005

4. Copper-Catalyzed Bromination of C(sp³ )-H Bonds Distal to Functional Groups.

Authors: Tao Liu; Michael C Myers; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-11-29 Impact factor: 15.336

5. Site-selective aliphatic C-H bromination using N-bromoamides and visible light.

Authors: Valerie A Schmidt; Ryan K Quinn; Andrew T Brusoe; Erik J Alexanian
Journal: J Am Chem Soc Date: 2014-10-03 Impact factor: 15.419

6. Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization.

Authors: Ramesh Giri; Masayuki Wasa; Steven P Breazzano; Jin-Quan Yu
Journal: Org Lett Date: 2006-12-07 Impact factor: 6.005

7. Pd-catalyzed cross-coupling reactions of alkyl halides.

Authors: Nobuaki Kambe; Takanori Iwasaki; Jun Terao
Journal: Chem Soc Rev Date: 2011-07-25 Impact factor: 54.564

8. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

Authors: Masayuki Wasa; Kelvin S L Chan; Xing-Guo Zhang; Jian He; Masanori Miura; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2012-11-05 Impact factor: 15.419

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. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

Authors: Ru-Yi Zhu; Jian He; Xiao-Chen Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2014-09-15 Impact factor: 15.419

12 in total

1. Highly Versatile β-C(sp³)-H Iodination of Ketones Using a Practical Auxiliary.

Authors: Ru-Yi Zhu; Luo-Yan Liu; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2017-08-29 Impact factor: 15.419

2. An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

Authors: Qing-Lan Pei; Guan-Da Che; Ru-Yi Zhu; Jian He; Jin-Quan Yu
Journal: Org Lett Date: 2017-11-03 Impact factor: 6.005

3. Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Authors: Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal: Angew Chem Int Ed Engl Date: 2017-12-07 Impact factor: 15.336

Review 4. 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

5. Mechanochemical halogenation of unsymmetrically substituted azobenzenes.

Authors: Dajana Barišić; Mario Pajić; Ivan Halasz; Darko Babić; Manda Ćurić
Journal: Beilstein J Org Chem Date: 2022-06-15 Impact factor: 2.544

6. Palladium-Catalyzed Enantioselective β-C(sp³)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

Authors: Erika L Lucas; Nelson Y S Lam; Zhe Zhuang; Hau Sun Sam Chan; Daniel A Strassfeld; Jin-Quan Yu
Journal: Acc Chem Res Date: 2022-01-25 Impact factor: 24.466

Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp³)-H Bonds.

1. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Review 2. Nature's inventory of halogenation catalysts: oxidative strategies predominate.

3. Sulfoximine assisted Pd(II)-catalyzed bromination and chlorination of primary β-C(sp3)-H bond.

4. Copper-Catalyzed Bromination of C(sp³ )-H Bonds Distal to Functional Groups.

5. Site-selective aliphatic C-H bromination using N-bromoamides and visible light.

6. Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization.

7. Pd-catalyzed cross-coupling reactions of alkyl halides.

8. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

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

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

1. Highly Versatile β-C(sp³)-H Iodination of Ketones Using a Practical Auxiliary.

2. An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

3. Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Review 4. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

5. Mechanochemical halogenation of unsymmetrically substituted azobenzenes.

6. Palladium-Catalyzed Enantioselective β-C(sp³)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

7. Palladium-Mediated C_γ -H Functionalization of Alicyclic Amines.

8. Site-selective bromination of sp³ C-H bonds.

9. Ligand-enabled ortho-C-H olefination of phenylacetic amides with unactivated alkenes.

10. β C-H di-halogenation via iterative hydrogen atom transfer.

Review 2. Nature's inventory of halogenation catalysts: oxidative strategies predominate.

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

Review 4. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 4. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.