Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes
Date
2022
Authors
Yang, Ke
Li, Zhi
Liu, Chong (TTU)
Li, Yunjian
Hu, Qingyue
Elsaid, Mazen (TTU)
Li, Bijin (TTU)
Das, Jayabrata
Dang, Yanfeng
Maiti, Debabrata
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
The transient directing group (TDG) strategy allowed long awaited access to the direct β-C(sp3)-H functionalization of unmasked aliphatic aldehydes via palladium catalysis. However, the current techniques are restricted to terminal methyl functionalization, limiting their structural scopes and applicability. Herein, we report the development of a direct Pd-catalyzed methylene β-C-H arylation of linear unmasked aldehydes by using 3-amino-3-methylbutanoic acid as a TDG and 2-pyridone as an external ligand. Density functional theory calculations provided insights into the reaction mechanism and shed light on the roles of the external and transient directing ligands in the catalytic transformation.
Description
© 2022 The Royal Society of Chemistry cc-by-nc
Keywords
Citation
Yang, K., Li, Z., Liu, C., Li, Y., Hu, Q., Elsaid, M., Li, B., Das, J., Dang, Y., Maiti, D., & Ge, H.. 2022. Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes. Chemical Science, 13(20). https://doi.org/10.1039/d2sc01677j