Iron-catalyzed aerobic oxidation of silyl ethers to carboxylic acids

被引：2

作者：

Lin, Zuizhi ^{[1
,2
]}

Ma, Shengming ^{[1
,3
,4
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, 220 Handan Lu, Shanghai 200433, Peoples R China

[4] Zhejiang Univ, Lab Mol Recognit & Synth, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 49期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

ALCOHOLS; DEPROTECTION;

D O I：

10.1039/d4cc01234h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct aerobic oxidation of silyl ethers to carboxylic acids has been developed. The mild reaction conditions lead to a broad range of functional group compatibility. Different types of silyl groups have been investigated and selective deprotective oxidation has been realized. The reaction could be conducted under air. Direct aerobic oxidation of silyl ethers to carboxylic acids using a series of mild reaction conditions has been developed.

引用

页码：6272 / 6275

页数：4

共 28 条

[1] The use of silyl groups in the synthesis of arabinofuranosides [J].

Abronina, P., I ;

Podvalnyy, N. M. ;

Kononov, L. O. .

RUSSIAN CHEMICAL BULLETIN, 2022, 71 (01) :6-29

[2] One-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants [J].

Barnych, Bogdan ;

Vatele, Jean-Michel .

SYNLETT, 2011, (14) :2048-2052

[3]

Bauman J. G., 2020, WO, Patent No. 2020069353

[4] Recent Advances in Silyl Protection of Alcohols [J].

Crouch, R. David .

SYNTHETIC COMMUNICATIONS, 2013, 43 (17) :2265-2279

[5] Iron-Catalyzed Aerobic Oxidation of Alcohols: Lower Cost and Improved Selectivity [J].

Jiang, Xingguo ;

Liu, Jinxian ;

Ma, Shengming .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (05) :825-835

[6] Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids [J].

Jiang, Xingguo ;

Ma, Shengming .

SYNTHESIS-STUTTGART, 2018, 50 (08) :1629-1639

[7] Iron-Catalyzed Aerobic Oxidation of Aldehydes: Single Component Catalyst and Mechanistic Studies [J].

Jiang, Xingguo ;

Zhai, Yizhan ;

Chen, Junyu ;

Han, Yulin ;

Yang, Zheng ;

Ma, Shengming .

CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (01) :15-19

[8] Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids [J].

Jiang, Xingguo ;

Zhang, Jiasheng ;

Ma, Shengming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) :8344-8347

[9] Novel method for efficient aerobic oxidation of silyl ethers to carbonyl compounds catalyzed with N-hydroxyphthalimide (NHPI) and lipophilic Co(II) complexes [J].

Karimi, B ;

Rajabi, J .

ORGANIC LETTERS, 2004, 6 (17) :2841-2844

[10] CHIRAL ORGANOSILICON COMPOUNDS .3. PERACID OXIDATION OF CHIRAL SILYL ENOL ETHERS [J].

KAYE, PT ;

LEARMONTH, RA .

SYNTHETIC COMMUNICATIONS, 1990, 20 (09) :1333-1338

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