Fluorotrifluoromethylation of Alkenes Mediated by a Hypervalent Trifluoromethyl-Iodine(III) Reagent

被引：0

作者：

Huang, Mingqin ^{[1
]}

Zhang, Chi ^{[1
]}

机构：

[1] Nankai Univ, Res Inst Elementoorgan Chem, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 19期

基金：

中国国家自然科学基金;

关键词：

COPPER-CATALYZED TRIFLUOROMETHYLATION; UNACTIVATED ALKENES; FLUORINATION; IODINE;

D O I：

10.1021/acs.orglett.4c01462

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present a novel strategy for synthesizing polyfluorinated compounds by the fluorotrifluoromethylation of olefins, which was achieved through a new trifluoromethyl-iodine(III) reagent TFNI-1. TFNI-1 was readily synthesized via a three-step process, and its structure was characterized by NMR spectroscopy and X-ray crystallography. It is shown by radical trapping and radical clock experiments that the reaction involves the CF3 radical intermediate.

引用

页码：4158 / 4162

页数：5

共 50 条

[21] Oligomeric Iodosylbenzene Sulfate: A Convenient Hypervalent Iodine Reagent for Oxidation of Organic Sulfides and Alkenes
Yusubov, Mehman S.
Yusubova, Rosa Y.
Funk, Tatyana V.
Chi, Ki-Whan
Zhdankin, Viktor V.
[J]. SYNTHESIS-STUTTGART, 2009, (15): : 2505 - 2508
[22] Novel and efficient synthesis of pyrroloiminoquinones using a hypervalent iodine(III) reagent
Kita, Y
Watanabe, H
Egi, M
Saiki, T
Fukuoka, Y
Tohma, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (04): : 635 - 636
[23] A fluorinating hypervalent iodine(III) reagent: 4-Iodotoluene difluoride
Quintiliano, Samir Augusto Pino
[J]. SYNLETT, 2007, (11) : 1797 - 1798
[24] New procedure for the preparation of highly sterically hindered alkenes using a hypervalent iodine reagent
ter Wiel, MKJ
Vicario, J
Davey, SG
Meetsma, A
Feringa, BL
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 28 - 30
[25] A convenient phosphoryloxylactonization of pentenoic acids with catalytic hypervalent iodine(III) reagent
Zhou, Zhong-Shi
He, Xue-Han
[J]. TETRAHEDRON LETTERS, 2010, 51 (18) : 2480 - 2482
[26] Oxidative Rearrangement of Secondary Amines Using Hypervalent Iodine(III)-Reagent
Murai, Kenichi
Kobayashi, Tetsuya
Miyoshi, Makoto
Fujioka, Hiromichi
[J]. ORGANIC LETTERS, 2018, 20 (08) : 2333 - 2337
[27] Silver-Mediated Oxidative Fluorotrifluoromethylation of Unactivated Alkenes
Yu, Wei
Xu, Xiu-Hua
Qing, Feng-Ling
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2039 - 2044
[28] Alkoxylation Followed by Iodination of Oxindole with Alcohols Mediated by Hypervalent Iodine Reagent in the Presence of Iodine
Kotagiri, Rajendraprasad
Adepu, Ramesh
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (33) : 4556 - 4564
[29] Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)
Celik, Murat
Alp, Cemalettin
Coskun, Betul
Gultekin, M. Serdar
Balci, Metin
[J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3659 - 3663
[30] Hypervalent iodine reagent-mediated reactions involving rearrangement processes
Zhang, Beibei
Li, Xiaoxian
Guo, Boying
Du, Yunfei
[J]. CHEMICAL COMMUNICATIONS, 2020, 56 (91) : 14119 - 14136

← 1 2 3 4 5 →