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

被引：17

作者：

Bai, Peng-Bo ^{[1
]}

Wu, Ming-Ying ^{[1
]}

Yang, Xin-Xin ^{[1
]}

Wang, Gang-Wei ^{[1
]}

Yang, Shang-Dong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2023年 / 34卷 / 05期

关键词：

Palladiumcatalyst; Axially chiral; Acetylation; Dibenzophosphorus oxide; ALPHA-AMINO-ACID; ORGANOPHOSPHORUS COMPOUNDS; CATALYZED OXIDATION; RAPID CONSTRUCTION; COUPLING REACTIONS; FUNCTIONALIZATION; ACETOXYLATION; C(SP(2))-H; ACTIVATION; ARYLATION;

D O I：

10.1016/j.cclet.2022.107894

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the first atroposelective C(sp2)-H bond acyloxylation enabled by a phosphine oxide di-recting 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 C -H functionalization reaction. (c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页数：4

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