Citation: Peng-Bo Bai, Ming-Ying Wu, Xin-Xin Yang, Gang-Wei Wang, Shang-Dong Yang. Phosphine oxide directing-group-enabled atroposelective C–H bond acyloxylation via an eight-membered palladacycle intermediate[J]. Chinese Chemical Letters, ;2023, 34(5): 107894. doi: 10.1016/j.cclet.2022.107894 shu

Phosphine oxide directing-group-enabled atroposelective C–H bond acyloxylation via an eight-membered palladacycle intermediate

a.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

yangshd@lzu.edu.cn

Received Date: 18 July 2022
Revised Date: 5 October 2022
Accepted Date: 7 October 2022
Available Online: 12 October 2022

Figures(5)

Herein, we report the first atroposelective C(sp²)–H bond acyloxylation enabled by a phosphine oxide directing group. Uniquely, this transformation is shown to proceed through an eight-membered palladacycle intermediate, as opposed to the kinetically and thermodynamically favored five-membered palladacycle intermediate. Additionally, L-pGlu-OH, a cheap and abundant chiral amino acid derivative, was identified as the best chiral ligand to promote this atroposelective remote CH functionalization reaction.
- Palladiumcatalyst,
- Axially chiral,
- Acetylation,
- Dibenzophosphorus oxide
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