Hydroaminomethylation of Olefins with Aminomethyltrifluoroborate by Photoredox Catalysis

被引：100

作者：

Miyazawa, Kazuki ^{[1
]}

Koike, Takashi ^{[1
]}

Akita, Munetaka ^{[1
]}

机构：

[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 13期

关键词：

amino acids; aminomethylation; electron transfer; photocatalysis; photochemistry; VISIBLE-LIGHT PHOTOREDOX; CROSS-COUPLING REACTIONS; BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE; ELECTRON-DEFICIENT ALKENES; C-C; COMBINING PHOTOREDOX; DUAL CATALYSIS; EASY ACCESS; ARYL; ARYLATION;

D O I：

10.1002/adsc.201400556

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A photocatalytic hydroaminomethylation of olefins with N-protected aminomethyltrifluoroborates has been developed. This methodology provides a new strategy for the introduction of a primary aminomethyl group onto electron-deficient C=C bonds. This reaction constitutes a facile entry into synthetically useful gamma-aminobutyric acid (GABA) derivatives such as baclofen.

引用

页码：2749 / 2755

页数：7

共 67 条

[1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].

Allen, Laura J. ;

Cabrera, Pablo J. ;

Lee, Melissa ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610

[2] 3-THIENYLAMINOBUTYRIC AND 3-FURYLAMINOBUTYRIC ACIDS - SYNTHESIS AND BINDING GABA-B RECEPTOR STUDIES [J].

BERTHELOT, P ;

VACCHER, C ;

FLOUQUET, N ;

DEBAERT, M ;

LUYCKX, M ;

BRUNET, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2557-2560

[3] 1-ARYL-2-(AMINOMETHYL)CYCLOPROPANECARBOXYLIC ACID-DERIVATIVES - A NEW SERIES OF POTENTIAL ANTIDEPRESSANTS [J].

BONNAUD, B ;

COUSSE, H ;

MOUZIN, G ;

BRILEY, M ;

STENGER, A ;

FAURAN, F ;

COUZINIER, JP .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :318-325

[4]

Cai S., 2012, ANGEW CHEM, V124, P8174

[5] Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals [J].

Cai, Shunyou ;

Zhao, Xinyang ;

Wang, Xinbo ;

Liu, Qisong ;

Li, Zigang ;

Wang, David Zhigang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8050-8053

[6] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].

Condie, Allison G. ;

Gonzalez-Gomez, Jose C. ;

Stephenson, Corey R. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+

[7] QSAR and molecular modeling studies of baclofen analogues as GABAB agonists.: Insights into the role of the aromatic moiety in GABAB binding and activation [J].

Costantino, G ;

Macchiarulo, A ;

Guadix, AE ;

Pellicciari, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (11) :1827-1832

[8] Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides [J].

Devulapally, Rammohan ;

Fleury-Bregeot, Nicolas ;

Molander, Gary A. ;

Seapy, Dave G. .

TETRAHEDRON LETTERS, 2012, 53 (09) :1051-1055

[9] Photochemistry and photophysics of coordination compounds: Iridium [J].

Flamigni, Lucia ;

Barbieri, Andrea ;

Sabatini, Cristiana ;

Ventura, Barbara ;

Barigelletti, Francesco .

PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 :143-203

[10] Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light [J].

Freeman, David B. ;

Furst, Laura ;

Condie, Allison G. ;

Stephenson, Corey R. J. .

ORGANIC LETTERS, 2012, 14 (01) :94-97

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