N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

被引：48

作者：

Chevallier, Floris ^{[1
]}

Halauko, Yury S. ^{[2
]}

Pecceu, Christelle ^{[1
]}

Nassar, Ibrahim F. ^{[1
]}

Dam, To Uyen ^{[1
]}

Roisnel, Thierry ^{[3
]}

Matulis, Vadim E. ^{[4
]}

Ivashkevich, Oleg A. ^{[4
]}

Mongin, Florence ^{[1
]}

机构：

[1] Univ Rennes 1, UMR 6510, CNRS, F-35042 Rennes, France

[2] Belarusian State Univ, Dept Electrochem, Minsk 220030, BELARUS

[3] Univ Rennes 1, CNRS, Ctr Diffractometrie 10, UMR 6226, F-35042 Rennes, France

[4] Belarusian State Univ, Res Inst Physicochem Problems, Minsk 220030, BELARUS

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 12期

关键词：

MEDIATED ZINCATION; ORTHO-LITHIATION; 1-PHENYLPYRAZOLE; CHEMISTRY; ARYLATION; LIGANDS; HALIDES;

D O I：

10.1039/c1ob05267e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N-aryl and N-heteroaryl pyrazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination. Mono-, di-, and tri-iodides have been obtained after subsequent trapping with iodine, depending on the substrate and on the quantity of base used. The results have been discussed in the light of the CH acidities of the substrates, determined both in the gas phase and in THF solution using the DFT B3LYP method.

引用

页码：4671 / 4684

页数：14

共 4 条

[1] Computed CH Acidity of Biaryl Compounds and Their Deprotonative Metalation by Using a Mixed Lithium/Zinc-TMP Base
Kadiyala, Raghu Ram
Tilly, David
Nagaradja, Elisabeth
Roisnel, Thierry
Matulis, Vadim E.
Ivashkevich, Oleg A.
Halauko, Yury S.
Chevallier, Floris
Gros, Philippe C.
Mongin, Florence
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7944 - 7960
[2] Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium-zinc base and regioselectivity-computed CH acidity relationship
Messaoud, Mohamed Yacine Ameur
Bentabed-Ababsa, Ghenia
Hedidi, Madani
Derdour, Aicha
Chevallier, Floris
Halauko, Yury S.
Ivashkevich, Oleg A.
Matulis, Vadim E.
Picot, Laurent
Thiery, Valerie
Roisnel, Thierry
Dorcet, Vincent
Mongin, Florence
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1475 - 1485
[3] Deproto-metallation using mixed lithium-zinc and lithium-copper bases and computed CH acidity of 2-substituted quinolines
Marquise, Nada
Bretel, Guillaume
Lassagne, Frederic
Chevallier, Floris
Roisnel, Thierry
Dorcet, Vincent
Halauko, Yury S.
Ivashkevich, Oleg A.
Matulis, Vadim E.
Gros, Philippe C.
Mongin, Florence
RSC ADVANCES, 2014, 4 (38) : 19602 - 19612
[4] Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles
Nagaradja, Elisabeth
Chevallier, Floris
Roisnel, Thierry
Dorcet, Vincent
Halauko, Yury S.
Ivashkevich, Oleg A.
Matulis, Vadim E.
Mongin, Florence
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (09) : 1475 - 1487

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