Copper-Catalyzed Aerobic Oxidative Trifluoromethylation of H-Phosphonates Using Trimethyl(trifluoromethyl)silane

被引：13

作者：

Chu, Lingling ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 10期

基金：

中国国家自然科学基金;

关键词：

copper catalysis; phosphonates; trifluoromethylation; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; MULTISUBSTRATE ANALOG INHIBITORS; MEDIATED TRIFLUOROMETHYLATION; DIFLUOROMETHYLENEPHOSPHONATE ANALOG; REDUCTIVE ELIMINATION; FACILE SYNTHESIS; BOND FORMATION; ARYL IODIDES; ARENES; FLUORINATION;

D O I：

10.1055/s-0031-1290806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-catalyzed aerobic oxidative trifluoromethylation of readily accessible H-phosphonates was demonstrated for the first time. This method not only provides an alternative method for the facile synthesis of a series of biologically important CF3-phosphonates, but also demonstrates the first example of the efficient construction of a P-CF3 bond via transition-metal catalysis.

引用

页码：1521 / 1525

页数：5

共 76 条

[1] Arnone A, 1998, SYNTHESIS-STUTTGART, P1511
[2] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV)
Ball, Nicholas D.
Kampf, Jeff W.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2878 - +
[3] Ready access to fluorinated phosphonate mimics of secondary phosphates. Synthesis of the (alpha,alpha-difluoroalkyl) phosphonate analogues of L-phosphoserine, L-phosphoallothreonine, and L-phosphothreonine
Berkowitz, DB
Eggen, M
Shen, QR
Shoemaker, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4666 - 4675
[4] Bin Y., 1996, TETRAHEDRON, V52, P9963
[5] BURTON DJ, 1979, SYNTHESIS-STUTTGART, P615
[6] Fluorinated ylides and related compounds
Burton, DJ
Yang, ZY
Qiu, WM
[J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1641 - 1715
[7] SYNTHESIS OF A DIFLUOROMETHYLENEPHOSPHONATE ANALOG OF GLYCEROL-3-PHOSPHATE - A SUBSTRATE FOR NADH LINKED GLYCEROL-3-PHOSPHATE DEHYDROGENASE
CHAMBERS, RD
JAOUHARI, R
OHAGAN, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) : 1169 - 1170
[8] FLUORINE IN ENZYME CHEMISTRY .2. THE PREPARATION OF DIFLUOROMETHYLENEPHOSPHONATE ANALOGS OF GLYCOLYTIC PHOSPHATES - APPROACHING AN ISOSTERIC AND ISOELECTRONIC PHOSPHATE MIMIC
CHAMBERS, RD
JAOUHARI, R
OHAGAN, D
[J]. TETRAHEDRON, 1989, 45 (16) : 5101 - 5108
[9] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
Cho, Eun Jin
Senecal, Todd D.
Kinzel, Tom
Zhang, Yong
Watson, Donald A.
Buchwald, Stephen L.
[J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
[10] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes
Chu, Lingling
Qing, Feng-Ling
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 1298 - 1304

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