Iodine-Mediated Fluorination of Alkenes with an HF Reagent: Regioselective Synthesis of 2-Fluoroalkyl Iodides

被引：6

作者：

Kitamura, Tsugio ^{[1
]}

Komoto, Ryuichi ^{[1
]}

Oyamada, Juzo ^{[1
]}

Higashi, Masahiro ^{[2
]}

Kishikawa, Yosuke ^{[2
]}

机构：

[1] Saga Univ, Dept Chem & Appl Chem, Saga 8408502, Japan

[2] Daikin Ind Ltd, Settsu, Osaka 5668585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 24期

关键词：

IODOFLUORINATION;

D O I：

10.1021/acs.joc.1c02422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorination reaction of alkenes with iodine and HF center dot pyridine complex (pyr center dot 9HF) was performed under mild conditions in the presence of K2S2O8 or Na2S2O8 as an oxidant. Aliphatic and aromatic alkenes underwent iodofluorination to give the iodofluorinated products with high regioselectivity. The substitution reactions of the iodofluorinated product by nitrogen, sulfur, and oxygen nucleophiles indicated further applications as a building block for synthesis of 2-fluoroalkyl-substituted compounds.

引用

页码：18300 / 18303

页数：4

共 50 条

[41] SYNTHESIS OF 1H-ISOINDOL-3-AMINE DERIVATIVES BY IODINE-MEDIATED CYCLIZATION OF 2-VINYLBENZAMIDINE DERIVATIVES
Kobayashi, Kazuhiro
Horiuchi, Mai
Fukamachi, Shuhei
Konishi, Hisatoshi
HETEROCYCLES, 2009, 78 (03) : 669 - 677
[42] Iodine-Mediated Synthesis of 2-(Methylthio)-4H-chromen-4-ones and Study of Their Halogenation Reactions
Elagamy, Amr
Shaw, Ranjay
Shah, Chandan
Pratap, Ramendra
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9478 - 9489
[43] Molecular Iodine-Mediated Synthesis of 2-Azaanthraquinones from [3.3.3]Propellanes via a Metal-Free Rearrangement
Alizadeh, Abdolali
Bagherinejad, Akram
Khanpour, Mojtaba
SYNTHESIS-STUTTGART, 2021, 53 (21): : 4059 - 4067
[44] Molecular Iodine-Mediated Domino Reaction for the Synthesis of Benzamides, 2,2-Diazidobenzofuran-3(2H)-ones and Benzoxazolones
Rajendar, K.
Kant, Ruchir
Narender, T.
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3591 - 3596
[45] Synthesis of Iodo-IndoIoazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization Pathway±
Sharma, Sudhir K.
Mandadapu, Anil K.
Kumar, Brijesh
Kundu, Bijoy
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16): : 6798 - 6805
[46] Rongalite/iodine-mediated C(sp3)-H bond oximation and thiomethylation reaction of methyl ketones using copper nitrate as the [NO] reagent: synthesis of thiohydroximic acids
Wang, Miao
Ren, Hui-Ying
Pu, Xiao-Yu
Zhang, Xiao-Lu
Zhu, He-Ying
Wu, An-Xin
Zhao, Bang-Tun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (37) : 7623 - 7627
[47] Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
Krivokolysko, Bogdan S.
Dotsenko, Victor V.
Pakholka, Nikolay A.
Dakhno, Polina G.
Strelkov, Vladimir D.
Aksenov, Nicolai A.
Aksenova, Inna, V
Krivokolysko, Sergey G.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2023, 20 (03) : 609 - 628
[48] Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
Bogdan S. Krivokolysko
Victor V. Dotsenko
Nikolay A. Pakholka
Polina G. Dakhno
Vladimir D. Strelkov
Nicolai A. Aksenov
Inna V. Aksenova
Sergey G. Krivokolysko
Journal of the Iranian Chemical Society, 2023, 20 : 609 - 628
[49] Synthesis of 1-aryl-1H-indole derivatives by iodine-mediated cyclization of 2-(arylamino)styrene derivatives
Kobayashi, Kazuhiro
Miyamoto, Kazuna
Yamase, Tohru
Nakamura, Daizo
Morikawa, Osamu
Konishi, Hisatoshi
Bulletin of the Chemical Society of Japan, 2006, 79 (10): : 1580 - 1584
[50] Iodine-mediated synthesis of sulfur-bridged enaminones and chromones via double C(sp2)-H thiolation
Gao, Yong
Wei, Li
Liu, Yunyun
Wan, Jie-Ping
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (21) : 4631 - 4634

← 1 2 3 4 5 →