Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes

被引：5

作者：

Thon, Daniel ^{[1
]}

Fuerst, Michael C. D. ^{[1
]}

Altmann, Lisa-Marie ^{[1
]}

Heinrich, Markus R. ^{[1
]}

机构：

[1] Friedrich Alexander Univ Erlangen Nurnberg, Dept Chem & Pharm, Pharmaceut Chem, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

关键词：

Diazonium; Radical reaction; Carboamination; Carbohydroxylation; Biaryl; DIAZONIUM SALTS; ARYL DIAZONIUM; METAL-FREE; ARYLATION; CHEMISTRY; HETEROARENES; CATALYSIS; VERSATILE; ELECTRON; ANILINES;

D O I：

10.1016/j.tet.2018.05.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at - 84 degrees C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temperature, can be stored for at least 20 days. In addition, the slow melting of aryldiazonium-containing ice cubes can serve as an alternative to syringe pumps that are commonly used if a controlled addition of the diazonium salt to the reaction mixture is required. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5289 / 5294

页数：6

共 50 条

[21] Regioselectivity of Hydroxyl Radical Reactions with Arenes in Nonaqueous Solutions
Moores, Lee C.
Kaur, Devinder
Smith, Mathew D.
Poole, James S.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06): : 3260 - 3269
[22] Reactions of aryldiazonium tetrafluoroborates with vinylbutyl ether in the presence of chlorides, bromides, alkali metal thiocyanates and ammonium
Grishchuk, BD
Kudrik, EY
Gorbovoi, PM
Ganushchak, NI
Zagrichuk, GY
Kaspruk, BI
ZHURNAL OBSHCHEI KHIMII, 1996, 66 (04): : 639 - 642
[23] REACTION OF BETA-HALOGENSTYRENES WITH ARYLDIAZONIUM CHLORIDES
OBUSHAK, ND
LYAKHOVICH, MB
GANUSHCHAK, NI
BILAYA, EE
ZHURNAL ORGANICHESKOI KHIMII, 1983, 19 (07): : 1545 - 1545
[24] FREE RADICAL ADDITION REACTIONS .1. REACTION OF TRI- DI- + MONO-CHLOROMETHANESULOHONYL CHLORIDES WITH ALKENES
GOLDWHITE, H
HARRIS, C
GIBSON, MS
TETRAHEDRON, 1964, 20 (06) : 1613 - &
[25] HYDROQUINONE AS A REDUCING AGENT FOR CONVERSION OF ARYLDIAZONIUM SALTS INTO ARENES
MCDONALD, RN
RICHMOND, JM
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (17) : 605 - 606
[26] Free Radical Addition Reactions of Allylic Sulfones to Alkenes
Tetrahedron, 18 (6493):
[27] Free radical addition reactions of allylic sulfones to alkenes
Harvey, IW
Phillips, ED
Whitham, GH
TETRAHEDRON, 1997, 53 (18) : 6493 - 6508
[28] Empirical rate rules for hydroxyl radical reactions with alkenes
Liu, Dapeng
Farooq, Aamir
COMBUSTION AND FLAME, 2025, 272
[29] Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation
Sun, Li
Wang, Liwei
Alhumade, Hesham
Yi, Hong
Cai, Hu
Lei, Aiwen
ORGANIC LETTERS, 2021, 23 (20) : 7724 - 7729
[30] THE META PHOTOCYCLOADDITION OF ARENES TO ALKENES
CORNELISSE, J
CHEMICAL REVIEWS, 1993, 93 (02) : 615 - 669

← 1 2 3 4 5 →