The preparation of (EtO)2P(O)CFHZnBr and (EtO)2P(O)CFHCu and their utility in the preparation of functionalized α-fluorophosphonates

被引：41

作者：

Zhang, X ^{[1
]}

Qiu, WM ^{[1
]}

Burton, DJ ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(99)00305-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organometallic reagent, (EtO)(2)P(O)CFHZnBr, was generated in situ in excellent yields via the reaction of (EtO)(2)P(O)CFHBr with zinc metal. Metathesis with Cu(I)Br gate (EtO)(2)P(O)CFHCu. The reagents exhibit excellent reactivity with substrates, such as allyl halides, alkynyl halides, vinyl halides, aryl halides and acyl or phosphoryl halides, and provide a useful one flask route to functionalized alpha-fluorophosphonates. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2681 / 2684

页数：4

共 20 条

[1] DEHYDROGENATION OF A PHOSPHONATE SUBSTRATE ANALOG BY GLYCEROL 3-PHOSPHATE DEHYDROGENASE
ADAMS, PR
HARRISON, R
INCH, TD
[J]. BIOCHEMICAL JOURNAL, 1974, 141 (03) : 729 - 732
[2] Efficient syntheses of (alpha-fluoropropargyl)phosphonate esters
Benayoud, F
deMendonca, DJ
Digits, CA
Moniz, GA
Sanders, TC
Hammond, GB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) : 5159 - 5164
[3] Synthesis of α-fluoro-β,γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl)phosphonate
Benayoud, F
Chen, L
Moniz, GA
Zapata, AJ
Hammond, GB
[J]. TETRAHEDRON, 1998, 54 (51) : 15541 - 15554
[4] SYNTHESIS OF ALPHA-FLUOROVINYLPHOSPHONATES
BLACKBURN, GM
PARRATT, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1417 - 1424
[5] SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 913 - 917
[6] STEREOSELECTIVE SYNTHESES OF THE METHYLENE-PHOSPHONATE AND ALPHA-FLUOROMETHYLENE-PHOSPHONATE ANALOGS OF 2-PHOSPHO-D-GLYCERIC ACID
BLACKBURN, GM
RASHID, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 317 - 319
[7] BLACKBURN GM, 1986, CHEM SCRIPTA, V26, P21
[8] Introduction of alpha-fluorophosphonomethyl ether functionality and its application to the synthesis of fluorinated acyclic phosphonate nucleosides
Chen, W
Flavin, MT
Filler, R
Xu, ZQ
[J]. TETRAHEDRON LETTERS, 1996, 37 (50) : 8975 - 8978
[9] CHENG PJ, 1974, BIOCHIM BIOPHYS ACTA, V341, P85, DOI 10.1016/0005-2744(74)90068-0
[10] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES
ENGEL, R
[J]. CHEMICAL REVIEWS, 1977, 77 (03) : 349 - 367

← 1 2 →