Room Temperature Deoxyfluorination of Benzaldehydes and α-Ketoesters with Sulfuryl Fluoride and Tetramethylammonium Fluoride

被引：45

作者：

Melvin, Patrick R. ^{[1
]}

Ferguson, Devin M. ^{[1
]}

Schimler, Sydonie D. ^{[1
]}

Bland, Douglas C. ^{[2
]}

Sanford, Melanie S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48109 USA

[2] DowDuPont, Div Agr, Corteva Agrisci, CP PD&P Proc Chem, 9330 Zionsville Rd, Indianapolis, IN 46268 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

关键词：

PALLADIUM-CATALYZED DIFLUOROMETHYLATION; COPPER-MEDIATED DIFLUOROMETHYLATION; ARYL HALIDES; CHLORIDES; BROMIDES; IODIDES;

D O I：

10.1021/acs.orglett.9b00054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the room temperature Wdeoxyfluorination of benzaldehydes and alpha-ketoesters using sulfuryl fluoride and Me4NF is described. A large scope of aryl and heteroaryl substrates is demonstrated, and this method compares favorably to other common deoxyfluorination methods for many substrates.

引用

页码：1350 / 1353

页数：4

共 39 条

[1] Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent [J].

Aikawa, Kohsuke ;

Serizawa, Hiroki ;

Ishii, Koki ;

Mikami, Koichi .

ORGANIC LETTERS, 2016, 18 (15) :3690-3693

[2] Synthesis, Reactivity, and Catalytic Applications of Isolable (NHC)Cu(CHF2) Complexes [J].

Bour, James R. ;

Kariofillis, Stavros K. ;

Sanford, Melanie S. .

ORGANOMETALLICS, 2017, 36 (07) :1220-1223

[3] The Guareschi-Thorpe Cyclization Revisited - An Efficient Synthesis of Substituted 2,6-Dihydroxypyridines and 2,6-Dichloropyridines [J].

Eriksson, Magnus C. ;

Zeng, Xingzhong ;

Xu, Jinghua ;

Reeves, Diana C. ;

Busacca, Carl A. ;

Farina, Vittorio ;

Senanayake, Chris H. .

SYNLETT, 2018, 29 (11) :1455-1460

[4] Copper-Mediated Difluoromethylation of Aryl and Vinyl Iodides [J].

Fier, Patrick S. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5524-5527

[5] A New Method for Aromatic Difluoromethylation: Copper-Catalyzed Cross-Coupling and Decarboxylation Sequence from Aryl Iodides [J].

Fujikawa, Kenichi ;

Fujioka, Yasutaka ;

Kobayashi, Akira ;

Amii, Hideki .

ORGANIC LETTERS, 2011, 13 (20) :5560-5563

[6] Synthesis of gem-difluorides from aldehydes using DFMBA [J].

Furuya, T ;

Fukuhara, T ;

Hara, S .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (05) :721-725

[7] Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes [J].

Ge, Shaozhong ;

Chaladaj, Wojciech ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4149-4152

[8] Cooperative dual palladium/silver catalyst for direct difluoromethylation of aryl bromides and iodides [J].

Gu, Yang ;

Leng, Xuebing ;

Shen, Qilong .

NATURE COMMUNICATIONS, 2014, 5

[9] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

[10] 2,2-difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent [J].

Hayashi, H ;

Sonoda, H ;

Fukumura, K ;

Nagata, T .

CHEMICAL COMMUNICATIONS, 2002, (15) :1618-1619

← 1 2 3 4 →