N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols withC-Nucleophiles under Solvent-Free Reaction Conditions

被引：5

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：

CATALYSTS | 2020年 / 10卷 / 08期

关键词：

alcohols; N-iodosuccinimide; C-C coupling; solvent-free reactions; green chemistry; SUBSTITUTION; ALKYLATION;

D O I：

10.3390/catal10080850

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

C-C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C-C bond formation, we reportN-iodosuccinimide (NIS) as the most effective precatalyst among theN-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.

引用

页数：8

共 50 条

[11] The Mannich-type reaction between N,O-acetals and carbon nucleophiles under solvent-free conditions
Matsumura, Y
Ikeda, T
Onomura, O
HETEROCYCLES, 2006, 67 (01) : 113 - 117
[12] Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions
Gribanov, Pavel S.
Golenko, Yulia D.
Topchiy, Maxim A.
Minaeva, Lidiya I.
Asachenko, Andrey F.
Nechaev, Mikhail S.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (01) : 120 - 125
[13] Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions
Pravst, Igor
Zupan, Marko
Stavber, Stojan
TETRAHEDRON, 2008, 64 (22) : 5191 - 5199
[14] Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions
Jereb, Marjan
Vrazic, Dejan
Zupan, Marko
TETRAHEDRON LETTERS, 2009, 50 (20) : 2347 - 2352
[15] Modified palladium-catalyzed sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions
Liang, Y
Xie, YX
Li, JH
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 379 - 381
[16] Addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions
de Godoy, Luiz Antonio F.
Camilo, Nilton Soares
Pilli, Ronaldo Aloise
TETRAHEDRON LETTERS, 2006, 47 (45) : 7853 - 7856
[17] Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions
Zhang, Furen
Li, Chunmei
Qi, Chenze
TETRAHEDRON-ASYMMETRY, 2013, 24 (07) : 380 - 388
[18] Selective Direct N-Alkylation of Amines with Alcohols using Iron(III) Phthalocyanine Chloride under Solvent-Free Conditions
Minakawa, Maki
Okubo, Masataka
Kawatsura, Motoi
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (12) : 1680 - 1682
[19] Solvent-free palladium-catalyzed C-O cross-coupling of (hetero)aryl halides with primary alcohols
Rzhevskiy, Sergey A.
Topchiy, Maxim A.
Bogachev, Vasilii N.
Minaeva, Lidiya I.
Cherkashchenko, Ilia R.
V. Lavrov, Konstantin
Sterligov, Grigorii K.
Nechaev, Mikhail S.
Asachenko, Andrey F.
MENDELEEV COMMUNICATIONS, 2022, 32 (02) : 258 - 259
[20] Direct Regioselective Alkylation of Non-Basic Heterocycles with Alcohols and Cyclic Ethers through a Dehydrogenative Cross-Coupling Reaction under Metal-Free Conditions
Kianmehr, Ebrahim
Fardpour, Maryam
Khan, Khalid Mohammed
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2661 - 2668

← 1 2 3 4 5 →