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Literature DB >> 30859828

Palladium-Catalyzed β-C-H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group.

Cong Dong¹, Liangfei Wu¹, Jianwei Yao¹, Kun Wei¹.

Abstract

This paper describes a new amino-amide-based transient directing group (TDG). The TDG can exhibit better performance in the Pd-catalyzed arylation of aliphatic aldehydes and ketones. This reaction showed good substrate compatibility and regioselectivity. The results indicated that 3-amino- N-isopropylpropionamide was more beneficial to the β-arylation of aliphatic aldehydes than other TDGs under relatively mild conditions.

Entities: Chemical Gene

Year: 2019 PMID： 30859828 DOI： 10.1021/acs.orglett.9b00366

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Transient Directing Group Enabled Pd-catalyzed γ-C(sp³)-H Oxygenation of Alkyl Amines.

Authors: Yan-Qiao Chen; Yongwei Wu; Zhen Wang; Jennifer X Qiao; Jin-Quan Yu
Journal: ACS Catal Date: 2020-04-24 Impact factor: 13.084

2. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

Authors: Han Seul Park; Zhoulong Fan; Ru-Yi Zhu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-06-05 Impact factor: 15.336

3. Pd^II-Catalyzed Site-selective β- and γ-C(sp³)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

Authors: Yi-Hao Li; Yuxin Ouyang; Nikita Chekshin; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2022-03-14 Impact factor: 16.383

Palladium-Catalyzed β-C-H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group.

1. Transient Directing Group Enabled Pd-catalyzed γ-C(sp³)-H Oxygenation of Alkyl Amines.

2. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

3. Pd^II-Catalyzed Site-selective β- and γ-C(sp³)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

4. Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.

5. Pd^II -Catalyzed Enantioselective C(sp³ )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

6. A dual role for acetohydrazide in Pd-catalyzed controlled C(sp³)-H acetoxylation of aldehydes.

Palladium-Catalyzed β-C-H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group.

1. Transient Directing Group Enabled Pd-catalyzed γ-C(sp3)-H Oxygenation of Alkyl Amines.

2. Distal γ-C(sp3 )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

3. PdII-Catalyzed Site-selective β- and γ-C(sp3)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

4. Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.

5. PdII -Catalyzed Enantioselective C(sp3 )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

6. A dual role for acetohydrazide in Pd-catalyzed controlled C(sp3)-H acetoxylation of aldehydes.

1. Transient Directing Group Enabled Pd-catalyzed γ-C(sp³)-H Oxygenation of Alkyl Amines.

2. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

3. Pd^II-Catalyzed Site-selective β- and γ-C(sp³)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

5. Pd^II -Catalyzed Enantioselective C(sp³ )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

6. A dual role for acetohydrazide in Pd-catalyzed controlled C(sp³)-H acetoxylation of aldehydes.