Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides

被引：52

作者：

Sheng, Jie

Ni, Hui-Qi

Liu, Ge

Li, Yan

Wang, Xi-Sheng ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 17期

基金：

美国国家科学基金会;

关键词：

CROSS-COUPLING REACTIONS; CARBON BOND FORMATION; ARYLBORONIC ACIDS; (2-PYRIDYL)SULFONYL GROUP; BENZYLIC FLUORINATION; ASYMMETRIC CATALYSIS; FLUOROMETHYL IODIDE; MEDICINAL CHEMISTRY; EMISSION-TOMOGRAPHY; EFFICIENT SYNTHESIS;

D O I：

10.1021/acs.orglett.7b02012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combinatorial nickel-catalyzed cross-coupling between arylboronic acids and unactived 1-fluoro-1-iodoalkanes has been developed, which demonstrated high efficiency, mild conditions, and excellent functional-group compatibility. Readily available nitrogen and phosphine ligands were combined with a nitrogen source, which in situ generated a variety of easily tunable catalysts to promote the fluoroalkylation for broad scopes of both coupling partners. This new strategy on combinatorial catalysis offers new solutions for nickel-catalyzed cross-coupling reactions.

引用

页码：4480 / 4483

页数：4

共 69 条

[1] Suzuki-Miyaura Coupling of Aryl Chlorides with Arylboronic Acids Using the Morpholine-NiCl2 Catalyst System [J].

Abe, Taichi ;

Mino, Takashi ;

Watanabe, Kohei ;

Sakamoto, Masami .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (31) :6983-6991

[2] Facile Access to Fluoromethylated Arenes by Nickel-Catalyzed Cross-Coupling between Arylboronic Acids and Fluoromethyl Bromide [J].

An, Lun ;

Xiao, Yu-Lan ;

Min, Qiao-Qiao ;

Zhang, Xingang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (31) :9079-9083

[3] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070

[4] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[5] Cinchona-modified platinum catalysts: From ligand acceleration to technical processes [J].

Blaser, Hans-Ulrich ;

Studer, Martin .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1348-1356

[6] Photocatalyzed Benzylic Fluorination: Shedding "Light" on the Involvement of Electron Transfer [J].

Bloom, Steven ;

McCann, Michael ;

Lectka, Thomas .

ORGANIC LETTERS, 2014, 16 (24) :6338-6341

[7] Iron(II)-Catalyzed Benzylic Fluorination [J].

Bloom, Steven ;

Pitts, Cody Ross ;

Woltornist, Ryan ;

Griswold, Andrew ;

Holl, Maxwell Gargiulo ;

Lectka, Thomas .

ORGANIC LETTERS, 2013, 15 (07) :1722-1724

[8]

Booth J. B., 2008, PAT. Appl. Pub., Patent No. [US 2008/0161365 A1, 20080161365]

[9]

Brickner S. J., 2012, US Patent, Patent No. [US 2012/0065188, A1, 20120065188]

[10] The btp [2,6-bis(1,2,3-triazol-4-yl[pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry [J].

Byrne, Joseph P. ;

Kitchen, Jonathan A. ;

Gunnlaugsson, Thorfinnur .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) :5302-5325

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