Photofluorination of Aliphatic C-H Bonds Promoted by the Phthalimide Group

被引：47

作者：

Egami, Hiromichi ^{[1
]}

Masuda, Shuya ^{[1
]}

Kawato, Yuji ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 05期

关键词：

LIQUID-PHASE PHOTOFLUORINATION; YLIDE-FORMING PHOTOREACTIONS; VISIBLE-LIGHT; BENZYLIC FLUORINATION; RADICAL FLUORINATION; ELEMENTAL FLUORINE; C(SP(3))-H BONDS; TRIFLUOROMETHYLATION; PHOTOCHEMISTRY; DERIVATIVES;

D O I：

10.1021/acs.orglett.8b00133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aliphatic C-H fluorination of phthalimide derivatives with Selectfluor was investigated under photo irradiation conditions. The reaction did not require any additive or catalyst and afforded C-H fluorinated products in moderate to good yields. It is likely that the reaction site depends on the C-H bond energy, and this may be the reason for the good to high regioselectivity.

引用

页码：1367 / 1370

页数：4

共 59 条

[1] Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical [J].

Amaoka, Yuuki ;

Nagatomo, Masanori ;

Inoue, Masayuki .

ORGANIC LETTERS, 2013, 15 (09) :2160-2163

[2] 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

[3] A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination [J].

Bloom, Steven ;

Pitts, Cody Ross ;

Miller, David Curtin ;

Haselton, Nathan ;

Holl, Maxwell Gargiulo ;

Urheim, Ellen ;

Lectka, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) :10580-10583

[4] Ketones as directing groups in photocatalytic sp3 C-H fluorination [J].

Bume, Desta Doro ;

Pitts, Cody Ross ;

Ghorbani, Fereshte ;

Harry, Stefan Andrew ;

Capilato, Joseph N. ;

Siegler, Maxime A. ;

Lectka, Thomas .

CHEMICAL SCIENCE, 2017, 8 (10) :6918-6923

[5] Direct, visible light-sensitized benzylic C-H fluorination of peptides using dibenzosuberenone: selectivity for phenylalanine-like residues [J].

Bume, Desta Doro ;

Pitts, Cody Ross ;

Jokhai, Rayyan Trebonias ;

Lectka, Thomas .

TETRAHEDRON, 2016, 72 (40) :6031-6036

[6] Recent Advances in Radical Fluorination [J].

Chatalova-Sazepin, Claire ;

Hemelaere, Remy ;

Paquin, Jean-Francois ;

Sammis, Glenn M. .

SYNTHESIS-STUTTGART, 2015, 47 (17) :2554-2569

[7] NITROGEN-SUBSTITUTED PHTHALIMIDES - FLUORESCENCE, PHOSPHORESCENCE, AND MECHANISM OF PHOTOCYCLIZATION [J].

COYLE, JD ;

NEWPORT, GL ;

HARRIMAN, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (02) :133-137

[8] Protected Sphingosine from Phytosphingosine as an Efficient Acceptor in Glycosylation Reaction [J].

Di Benedetto, Roberta ;

Zanetti, Luca ;

Varese, Monica ;

Rajabi, Mehdi ;

Di Brisco, Riccardo ;

Panza, Luigi .

ORGANIC LETTERS, 2014, 16 (03) :952-955

[9] Benzylic C-H trifluoromethylation of phenol derivatives [J].

Egami, Hiromichi ;

Ide, Takafumi ;

Kawato, Yuji ;

Hamashima, Yoshitaka .

CHEMICAL COMMUNICATIONS, 2015, 51 (93) :16675-16678

[10] Asymmetric Fluorolactonization with a Bifunctional Hydroxyl Carboxylate Catalyst [J].

Egami, Hiromichi ;

Asada, Junshi ;

Sato, Kentaro ;

Hashizume, Daisuke ;

Kawato, Yuji ;

Hamashima, Yoshitaka .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10132-10135

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