Direct and convenient conversion of alcohols to fluorides

被引：92

作者：

Yin, JJ ^{[1
]}

Zarkowsky, DS ^{[1
]}

Thomas, DW ^{[1
]}

Zhao, MM ^{[1
]}

Huffman, MA ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Sharp & Dohme Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 09期

关键词：

D O I：

10.1021/ol049672a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Directly mixing primary, secondary, and tertiary alcohols with nC(4)F(9)SO(2)F-NR3(HF)(3)-NR3 in THF or MeCN results in convenient conversion to the corresponding fluorides in high yields. The readily available reagents are easy to handle, and the mild, almost neutral reaction conditions allow for excellent functional group compatibility. A NR3(HF)NR3 ratio of less than or equal to1:2 gives the highest reactivity.

引用

页码：1465 / 1468

页数：4

共 38 条

[1] Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters:: preparation of a versatile intermediate for synthesis of 2′-[18F]-fluoro-arabinonucleosides
Alauddin, MM
Conti, PS
Mathew, T
Fissekis, JD
Prakash, GKS
Watanabe, KA
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2000, 106 (01) : 87 - 91
[2] SYNTHESIS OF DEOXYHALOGENO SUGARS - REACTION OF HALIDE-IONS WITH 1,2,3,4-TETRA-O-ACETYL-6-O-[(TRIFLUOROMETHYL)SULFONYL]-BETA-D-GLUCOPYRANOSE
AMBROSE, MG
BINKLEY, RW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) : 674 - 677
[3] A FACILE CONVERSION OF PRIMARY OR SECONDARY ALCOHOLS WITH N-PERFLUOROBUTANESULFONYL FLUORIDE/1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE INTO THEIR CORRESPONDING FLUORIDES
BENNUASKALMOWSKI, B
VORBRUGGEN, H
[J]. TETRAHEDRON LETTERS, 1995, 36 (15) : 2611 - 2614
[4] Stable dialkyl ether/poly(hydrogen fluoride) complexes:: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent
Bucsi, I
Török, B
Marco, AI
Rasul, G
Prakash, GKS
Olah, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (26) : 7728 - 7736
[5] Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon
Chou, TS
Becke, LM
OToole, JC
Carr, MA
Parker, BE
[J]. TETRAHEDRON LETTERS, 1996, 37 (01) : 17 - 20
[6] DIALKYL-DELTA,DELTA-DIFLUOROBENZYLAMINES AND DIALKYL(TRIFLUOROMETHYL)-AMINES - NOVEL FLUORINATING REAGENTS
DMOWSKI, W
KAMINSKI, M
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1983, 23 (03) : 219 - 228
[7] ALKALI-METAL FLUORIDES AS EFFICIENT FLUORINATING AGENTS - ENANTIOCONTROLLED SYNTHESIS OF 2-FLUOROALKYL CARBOXYLATES AND 1-FLUOROALKYL BENZENES
FRITZLANGHALS, E
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (06) : 981 - 986
[8] SYNTHESIS OF OPTICALLY-ACTIVE 1-FLUOROALKYL BENZENES
FRITZLANGHALS, E
[J]. TETRAHEDRON LETTERS, 1994, 35 (12) : 1851 - 1854
[9] ET3N.2HF, A NEW CONVENIENT REAGENT FOR NUCLEOPHILIC FLUORINE DISPLACEMENT-REACTIONS
GIUDICELLI, MB
PICQ, D
VEYRON, B
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6527 - 6530
[10] 2,2-difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent
Hayashi, H
Sonoda, H
Fukumura, K
Nagata, T
[J]. CHEMICAL COMMUNICATIONS, 2002, (15) : 1618 - 1619

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