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

[31] Enantioselective reductive C-O bond cleavage driven by photoinduced electron transfer
Wang, Wen-Yao
Wang, Jing-Jun
Pan, Jia-Bin
Xiao, Li-Jun
Zhou, Qi-Lin
CHEM, 2024, 10 (12): : 3667 - 3677
[32] Fe-Catalyzed Electrochemical C-O Bond Cleavage of Ethers to Access Benzazoles from Ethers and o-Substituted Anilines
Lai, Yin-Long
Yang, Xiao
Wu, Si-Chao
Li, Xi-Yong
Gong, Yao-Xiong
Zhang, Sheng-Ling
Zhong, Rui-Min
Liao, Jian-Hua
Luo, Jian-Min
CHEMELECTROCHEM, 2022, 9 (19):
[33] Metal-free synthesis of ketonitriles via C-F bond cleavage
Gao, Ge
Li, Zhiping
NEW JOURNAL OF CHEMISTRY, 2023, 47 (13) : 6171 - 6175
[34] Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)-O/C(sp2)-S Bond Cleavage Strategy
Lia, Shen-Huan
Longa, Cheng-Yu
Yang, Xin-Ge
Wang, Xue-Qiang
SYNTHESIS-STUTTGART, 2021, 53 (20): : 3716 - 3724
[35] Axially Chiral Bridged Biaryls by Ni-Catalyzed Kinetic Asymmetric C-O Bond Cleavage
Fang, Yijun
Hu, Jiameng
Sun, Tingting
Zhou, Yu
Luo, Gen
Cao, Zhi-Chao
ACS CATALYSIS, 2024, 14 (11): : 8176 - 8183
[36] Recent developments in the metal-free synthesis of oxazoles
Wanjari, Pravin J.
Mehta, Kriti
Kudumula, Marudhvathi
Sharma, Rohit
Bharatam, Prasad, V
TETRAHEDRON, 2025, 169
[37] Palladium-Catalyzed Desulfitative Arylation by C-O Bond Cleavage of Aryl Inflates with Sodium Arylsulfinates
Zhou, Chao
Liu, Qingjiang
Li, Yaming
Zhang, Rong
Fu, Xinmei
Duan, Chunying
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 10468 - 10472
[38] Synthesis of (±)-Physovenine through Electrochemical C-O Bond Formation
Wang, Feijun
Frankowski, Kevin J. J.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (47)
[39] Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines
Wang, Guodong
Guo, Yanhui
Wan, Jieping
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 645 - 650
[40] Direct β-Acyloxylation of Enamines via PhIO-Mediated Intermolecular Oxidative C-O Bond Formation and Its Application to the Synthesis of Oxazoles
Liu, Xin
Cheng, Ran
Zhao, Feifei
Zhang-Negrerie, Daisy
Du, Yunfei
Zhao, Kang
ORGANIC LETTERS, 2012, 14 (21) : 5480 - 5483

← 1 2 3 4 5 →