Direct substitution of the hydroxy group of alcohols with N-nucleophiles mediated by the substoichiometric amount of SelectfluorTM F-TEDA-BF4 as a precatalyst under mild reaction conditions

被引：0

作者：

Ajvazi, Njomza ^{[1
]}

Stavber, Stojan ^{[1
,2
]}

机构：

[1] Jozef Stefan Int Postgrad Sch, Jamova 39, Ljubljana 1000, Slovenia

[2] Jozef Stefan Inst, Jamova 39, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON LETTERS | 2023年 / 115卷

关键词：

Alcohols; C -N bond formation; Cross; -coupling; Green chemistry; SelectfluorTMF-TEDA-BF4;

D O I：

10.1016/j.tetlet.2022.154318

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SelectfluorTM F-TEDA-BF4 was introduced, tested, and applied as an efficient, metal-free, and environmen-tally benign precatalyst for direct cross-coupling of various alcohols with N-nucleophiles under mild reaction conditions enhancing the green chemical profiles of these transformations. The scale-up proce-dure was achieved with an almost quantitative yield, confirming the presented method's synthetic appli-cability and potential for industrial application.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

共 8 条

[1] Mild and Efficient Iodine-Catalyzed Direct Substitution of Hydroxy Group of Alcohols with C- and N-Nucleophiles
Liu, Zhe
Wang, Dong
Chen, Yongjun
LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (01) : 73 - 80
[2] Selectfluor™ F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions
Khazaei, Ardeshir
Rahmati, Sadegh
Khalafi-nezhad, Ali
Saednia, Shahnaz
JOURNAL OF FLUORINE CHEMISTRY, 2012, 137 : 123 - 125
[3] Direct Cross-Coupling of Alcohols with O-Nucleophiles Mediated by N-Iodosuccinimide as a Precatalyst under Mild Reaction Conditions
Ajvazi, Njomza
Stavber, Stojan
CATALYSTS, 2021, 11 (07)
[4] The effect of reaction conditions on activation parameters for the mild introduction of fluorine into phenyl substituted alkenes with Selectfluor™ F-TEDA-BF4
Papez-Iskra, M
Zupan, M
Stavber, S
ACTA CHIMICA SLOVENICA, 2005, 52 (03) : 200 - 206
[5] An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using SelectfluorTM F-TEDA-BF4
Mohammad Reza Poor Heravi
ChineseChemicalLetters, 2010, 21 (12) : 1399 - 1402
[6] N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols withC-Nucleophiles under Solvent-Free Reaction Conditions
Ajvazi, Njomza
Stavber, Stojan
CATALYSTS, 2020, 10 (08)
[7] Direct boronation of allyl alcohols with diboronic acid using palladium pincer-complex catalysis.: A remarkably facile allylic displacement of the hydroxy group under mild reaction conditions
Olsson, VJ
Sebelius, S
Selander, N
Szabó, KJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) : 4588 - 4589
[8] Direct boronation of allyl alcohols with diboronic acid using palladium pincer-complex catalysis. A remarkably facile allylic displacement of the hydroxy group under mild reaction conditions
Olsson, Vilhelm J.
Sebelius, Sara
Selander, Nicklas
Szabo, Kalman J.
Journal of the American Chemical Society, 2006, 128 (14): : 4588 - 4589

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