Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups.ACS Catal. 2022 Sep 02; 12(17):10581-10586.AC
Abstract
Pd(II)-catalyzed γ-C(sp[3])-H (hetero)arylation of aliphatic ketones is developed using α-amino acid as transient directing groups (TDG). A variety of aliphatic ketones were (hetero)arylated at the γ-position via a 5,6-membered fused cyclopalladation intermediate to afford the remotely arylated products in up to 88% yield. The crucial ligand effect of 2-pyridone is further enhanced by reducing the loading of acid additives. Consequentially, the improved reactivity of this catalytic system has also made possible the cyclic γ-methylene C(sp[3])-H arylation of ketones. Mechanistic investigtigation and comparison to the γ-C-H arylation of aldehydes revealed a structural insight for designing site selective TDG.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
37305173
Citation
Li, Yi-Hao, et al. "Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled By Transient Directing Groups." ACS Catalysis, vol. 12, no. 17, 2022, pp. 10581-10586.
Li YH, Ouyang Y, Chekshin N, et al. Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups. ACS Catal. 2022;12(17):10581-10586.
Li, Y. H., Ouyang, Y., Chekshin, N., & Yu, J. Q. (2022). Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups. ACS Catalysis, 12(17), 10581-10586. https://doi.org/10.1021/acscatal.2c03400
Li YH, et al. Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled By Transient Directing Groups. ACS Catal. 2022 Sep 2;12(17):10581-10586. PubMed PMID: 37305173.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Pd[II]-Catalyzed γ-C(sp[3])-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups.
AU - Li,Yi-Hao,
AU - Ouyang,Yuxin,
AU - Chekshin,Nikita,
AU - Yu,Jin-Quan,
Y1 - 2022/08/15/
PY - 2023/6/12/medline
PY - 2023/6/12/pubmed
PY - 2023/6/12/entrez
KW - C−H activation
KW - Ketones
KW - Palladium
KW - arylation
KW - palladacycle
KW - pyridone ligands
KW - transient directing group
SP - 10581
EP - 10586
JF - ACS catalysis
JO - ACS Catal
VL - 12
IS - 17
N2 - Pd(II)-catalyzed γ-C(sp[3])-H (hetero)arylation of aliphatic ketones is developed using α-amino acid as transient directing groups (TDG). A variety of aliphatic ketones were (hetero)arylated at the γ-position via a 5,6-membered fused cyclopalladation intermediate to afford the remotely arylated products in up to 88% yield. The crucial ligand effect of 2-pyridone is further enhanced by reducing the loading of acid additives. Consequentially, the improved reactivity of this catalytic system has also made possible the cyclic γ-methylene C(sp[3])-H arylation of ketones. Mechanistic investigtigation and comparison to the γ-C-H arylation of aldehydes revealed a structural insight for designing site selective TDG.
SN - 2155-5435
UR - https://www.unboundmedicine.com/medline/citation/37305173/PdII_Catalyzed_γ_C_sp3__H__Hetero_Arylation_of_Ketones_Enabled_by_Transient_Directing_Groups_
DB - PRIME
DP - Unbound Medicine
ER -
