Synthesis of Aryl-methylene Ethers through Pd(0)-Catalyzed Coupling between Hydrobenzoxazoles and Dichloromethane

被引：3

作者：

Wang, Yinpeng ^{[1
]}

Zhao, Mingming ^{[1
]}

Peng, Jingke ^{[1
]}

Zheng, Hongxia ^{[1
]}

Xiong, Heng-Ying ^{[1
]}

Zhang, Guangwu ^{[1
]}

机构：

[1] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China

来源：

ORGANIC LETTERS | 2023年

基金：

中国国家自然科学基金;

关键词：

OXIDATIVE-ADDITION; PALLADIUM; KETIMINES; CARBENE; HALIDES; ACTIVATION; ANNULATION; COMPLEXES;

D O I：

10.1021/acs.orglett.3c00190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using dichloromethane (DCM) as the C1 feedstock, the first Pd(0)-catalyzed synthesis of aryl-methylene ether motifs from hydrobenzoxazoles (hydrothiazoles) has been reported. This protocol has exhibited an ample substrate scope (38 examples) and wide functional group tolerance. Aryl-methylene ether adducts have been successfully engaged in coupling with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM has served as a twofold electrophile for reaction with hydrobenzoxazoles via double C-Cl bond cleavage.

引用

页码：1458 / 1463

页数：6

共 31 条

[1]

Caron S., 2011, PRACTICAL SYNTHETIC, P237

[2] Palladium-catalysed hydroxylation and alkoxylation [J].

Enthaler, Stephan ;

Company, Anna .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4912-4924

[3] Metal-mediated C-O bond forming reactions in natural product synthesis [J].

Evano, Gwilherm ;

Wang, Jianjun ;

Nitelet, Antoine .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12) :2480-2499

[4] A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols [J].

Gowrisankar, Saravanan ;

Sergeev, Alexey G. ;

Anbarasan, Pazhamalai ;

Spannenberg, Anke ;

Neumann, Helfried ;

Beller, Matthias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) :11592-11598

[5] CHLOROCARBON ACTIVATION - CATALYTIC CARBONYLATION OF DICHLOROMETHANE AND CHLOROBENZENE [J].

HUSER, M ;

YOUINOU, MT ;

OSBORN, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (10) :1386-1388

[6] Palladium(0) complexes of diferrocenylmercury diphosphines: synthesis, X-ray structure analyses, catalytic isomerization, and C-Cl bond activation [J].

Kuate, Alain C. Tagne ;

Lalancette, Roger. A. ;

Bockfeld, Dirk ;

Tamm, Matthias ;

Jakle, Frieder .

DALTON TRANSACTIONS, 2021, 50 (13) :4512-4518

[7] Facile Oxidative Addition of Organic Halides to Heteroleptic and Homoleptic Pd0-N-Heterocyclic Carbene Complexes [J].

Lee, Jung-Hyun ;

Jeon, Hyeong-Tak ;

Kim, Yong-Joo ;

Lee, Kyung-Eun ;

Jang, Young Ok ;

Lee, Soon W. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (11) :1750-1761

[8] THE 1ST PALLADIUM(0) COMPLEX WITH ONLY SECONDARY PHOSPHINES AS LIGANDS AND ITS OXIDATIVE-ADDITION REACTIONS WITH CH2CL2 AND CHCL3, GIVING THE THERMALLY STABLE DERIVATIVES TRANS-[PDCL(R)(PBU(T)2H)2] (R = CH2CL, CHCL2) [J].

LEONI, P .

ORGANOMETALLICS, 1993, 12 (07) :2432-2434

[9] Methylenecyclopropane Annulation by Manganese(I)-Catalyzed Stereoselective C-H/C-C Activation [J].

Liang, Yu-Feng ;

Mueller, Valentin ;

Liu, Weiping ;

Muench, Annika ;

Stalke, Dietmar ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) :9415-9419

[10] Manganese-Catalyzed Synthesis of cis-β-Amino Acid Esters through Organometallic C-H Activation of Ketimines [J].

Liu, Weiping ;

Zell, Daniel ;

John, Michael ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :4092-4096

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