Metal free C-O bond cleavage: a new strategy for the synthesis of substituted oxazoles

被引：1

作者：

Li, Shengwang ^{[1
]}

Liu, Guiqin ^{[1
]}

Zhang, Zheyan ^{[1
]}

Chen, Ruiling ^{[2
]}

Tian, Haiying ^{[2
]}

Wang, Huifeng ^{[1
]}

Chen, Xiuling ^{[1
]}

机构：

[1] Hubei Univ Sci & Technol, Hubei Key Lab Radiat Chem & Funct Mat, Xianning 437100, Peoples R China

[2] Changzhi Med Coll, Sch Pharm, Changzhi 046000, Peoples R China

来源：

RSC ADVANCES | 2024年 / 14卷 / 38期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; ETHERS; OXYGENATION; CYCLIZATION; ACTIVATION; KETONES; AZOLES; ESTERS; CARBON;

D O I：

10.1039/d4ra05122j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A strategy for the efficient metal-free C-O bond cleavage of ester using amines for the synthesis of substituted oxazoles was developed for the first time. The synthesis proceeded smoothly under metal-free conditions, combining C-O bond cleavage as well as C-N and C-O bond formation in one pot to yield desired products in moderate to excellent yields, and accommodated a wide range of functional groups and substrates. A strategy for C-O bond cleavage of ester for the synthesis of substituted oxazoles was developed. The synthesis proceeded smoothly under metal-free conditions, combining C-O bond cleavage, C-N and C-O bond formation in one pot.

引用

页码：28210 / 28214

页数：5

共 50 条

[41] Palladium-Catalyzed Chemo- and Enantioselective C-O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis
Chen, Jianzhong
Zhang, Zhenfeng
Liu, Delong
Zhang, Wanbin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) : 8444 - 8447
[42] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
Lin, Zhiyang
Lan, Yun
Wang, Chuan
ACS CATALYSIS, 2019, 9 (01) : 775 - 780
[43] Metal-free, visible-light-induced C(sp2)-H functionalization/C-O bond formation for the synthesis of flavones using air as an oxidant
Bai, Yuntao
Yang, Manqiang
Lin, Shao-Xia
Borse, Rahul Anil
Thoke, Mahesh Bhagwan
Yuan, Daqiang
TETRAHEDRON LETTERS, 2023, 121
[44] Metal-free oxidative cleavage of the C-C bond in α-hydroxy-β-oxophosphonates
Battula, Satyanarayana
Kumar, Atul
Ahmed, Qazi Naveed
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (39) : 9953 - 9956
[45] Activating a Peroxo Ligand for C-O Bond Formation
Pilar del Rio, M.
Abril, Paula
Lopez, Jose A.
Sodupe, Mariona
Lledos, Agusti
Ciriano, Miguel A.
Tejel, Cristina
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) : 3037 - 3041
[46] Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage
Correa, Arkaitz
Martin, Ruben
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (20) : 7253 - 7256
[47] How and Why Does Ni0 Promote Smooth Etheric C-O Bond Cleavage and C-C Bond Formation? A Theoretical Study
Ogawa, Hiroyuki
Minami, Hiroki
Ozaki, Takashi
Komagawa, Shinsuke
Wang, Chao
Uchiyama, Masanobu
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (40) : 13904 - 13908
[48] A Metal-Free Tandem C-C/C-O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans
Reddy, Chada Raji
Reddy, Motatipally Damoder
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) : 106 - 116
[49] Cu-catalyzed coupling of unactivated tertiary alkyl alcohols with thiols via C-O bond cleavage
Xu, Bing
Ye, Yang
Lin, Ying
Bai, Renren
Ye, Xiang-Yang
Xie, Tian
TETRAHEDRON LETTERS, 2022, 89
[50] Salicylate-Directed C-O Bond Cleavage: Iron-Catalyzed Allylic Substitution with Grignard Reagents
Ma, Enlu
Jiang, Yifan
Chen, Yuanjin
Qi, Longying
Yan, Xiaoyu
Li, Zhiping
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (05) : 914 - 917

← 1 2 3 4 5 →