N-Trifluoromethylselenophthalimide, an Electrophilic Trifluoromethylselenolation Reagent and Its Application for the Synthesis of 4-Trifluoromethylselenolated Isoxazoles

被引：2

作者：

Wang, Jia ^{[1
]}

Lu, Xiao-Xiao ^{[1
]}

Yang, Run-Ping ^{[1
]}

Zhang, Bing-Bing ^{[1
]}

Xiang, Zhi-Hao ^{[1
]}

Li, Jia-Cheng ^{[1
]}

Liu, Lixia ^{[1
]}

Chao, Shujun ^{[1
]}

Shang, Xuefang ^{[1
]}

机构：

[1] Xinxiang Med Univ, Sch Basic Med Sci, Xinxiang 453003, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 47期

关键词：

SULFENYLATION; FLUORINE;

D O I：

10.1021/acs.orglett.3c03446

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new electrophilic trifluoromethylselenolation reagent, N-trifluoromethylselenophthalimide (Phth-SeCF3), was developed. A strategy for the synthesis of 4-trifluoromethylselenolated isoxazoles through electrophilic trifluoromethylselenolation cyclization has been established by using Phth-SeCF3 as an electrophilic reagent. Moreover, this protocol has the features of broad substrate scope, good functional group tolerance, and high yields.

引用

页码：8489 / 8494

页数：6

共 50 条

[1] Selenocyanobenziodoxolone: a practical electrophilic selenocyanation reagent and its application for solid-state synthesis of α-carbonyl selenocyanates
Xiao, Jun-An
Li, Yu-Chun
Cheng, Xiu-Liang
Chen, Wen-Qiang
Cui, Jian-Guo
Huang, Van-Min
Huang, Jun
Xiao, Qi
Su, Wei
Yang, Hua
[J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (12): : 1967 - 1971
[2] N-Trifluoromethylthiophthalimide: A Stable Electrophilic SCF3-Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation
Bootwicha, Teerawut
Liu, Xiangqian
Pluta, Roman
Atodiresei, Iuliana
Rueping, Magnus
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12856 - 12859
[3] DESIGN AND SYNTHESIS OF A CARBON-14 ELECTROPHILIC CYANATING REAGENT: 1-[14C]CYANOBENZOTRIAZOLE AND ITS APPLICATION IN ORGANIC SYNTHESIS
Ren, Sumei
Mcnamara, Paul
Koharski, David
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (5-6): : 247 - 250
[4] N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENT FOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES
TSUNODA, T
OTSUKA, J
YAMAMIYA, Y
ITO, S
[J]. CHEMISTRY LETTERS, 1994, (03) : 539 - 542
[5] Synthesis of N-Iodosuccinimide and Its Application in H2SO4 as Efficient Iodination Reagent for Deactivated Aromatic Compounds
V. K. Chaikovskii
V. I. Skorokhodov
V. D. Filimonov
[J]. Russian Journal of Organic Chemistry, 2001, 37 : 1503 - 1504
[6] Synthesis of N-iodosuccinimide and its application in H2SO4 as efficient iodination reagent for deactivated aromatic compounds
Chaikovskii, VK
Skorokhodov, VI
Filimonov, VD
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (10) : 1503 - 1504
[7] 4-METHYL-5-HYDROXYPYRIMIDINE AND ITS N-OXIDES - SYNTHESIS AND REACTIVITY IN ELECTROPHILIC SUBSTITUTION
GASHEV, SB
GOLTSOVA, LV
SMIRNOV, LD
LEZINA, VP
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1989, (05): : 636 - 640
[8] Synthesis of a new metallofluorecent reagent (3-carboxy-2-naphthylamine-N,N-diacetic acid) and its application
Miyahara, T
Ogai, H
Kitamura, H
Narita, K
Toyo'oka, T
[J]. YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1998, 118 (08): : 301 - 309
[9] Reagent for synthesis of secondary amines by two consecutive N-alkylations and its application to orthogonally protected spermidine
Grehn, L
Ragnarsson, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18): : 6557 - 6559
[10] Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction
Zhang, YC
Sammakia, T
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3139 - 3141

← 1 2 3 4 5 →