A mechanistic investigation of the Pd-catalyzed cross-coupling between N-tosylhydrazones and aryl halides

被引：10

作者：

Thomas, Gilian T. ^{[1
]}

Ronda, Kiera ^{[1
]}

McIndoe, J. Scott ^{[1
]}

机构：

[1] Univ Victoria, Victoria, BC, Canada

来源：

DALTON TRANSACTIONS | 2021年 / 50卷 / 43期

基金：

加拿大自然科学与工程研究理事会;

关键词：

REAGENTS; SONOGASHIRA;

D O I：

10.1039/d1dt03161a

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cross-coupling of N-tosylhydrazones and aryl halides forms carbon-carbon bonds, producing 1,1-disubstituted alkenes. Though it has proven extremely useful in several fields of chemistry, its mechanism remains experimentally unexplored. Combining benchtop NMR and real-time mass spectrometry afforded the ability to monitor the catalytic intermediates as well as the rate of product formation.

引用

收藏

页码：15533 / 15537

页数：5

相关论文

共 42 条

[1] Mechanistic features of the copper-free Sonogashira reaction from ESI-MS [J].

Ahmadi, Zohrab ;

Yunker, Lars P. E. ;

Oliver, Allen G. ;

McIndoe, J. Scott .

DALTON TRANSACTIONS, 2015, 44 (47) :20367-20375

[2] Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization [J].

Aziz, Jessy ;

Brion, Jean-Daniel ;

Alami, Mouad ;

Hamze, Abdallah .

RSC ADVANCES, 2015, 5 (91) :74391-74398

[3] Synthesis, biological evaluation, and structure-activity relationships of tri- and tetrasubstituted olefins related to isocombretastatin A-4 as new tubulin inhibitors [J].

Aziz, Jessy ;

Brachet, Etienne ;

Hamze, Abdallah ;

Peyrat, Jean-Francois ;

Bernadat, Guillaume ;

Morvan, Estelle ;

Bignon, Jerome ;

Wdzieczak-Bakala, Joanna ;

Desravines, Deborah ;

Dubois, Joelle ;

Tueni, Marie ;

Yassine, Ahmad ;

Brion, Jean-Daniel ;

Alami, Mouad .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (03) :430-442

[4] THE DECOMPOSITION OF TOLUENE-PARA-SULPHONYLHYDRAZONES BY ALKALI [J].

BAMFORD, WR ;

STEVENS, TS .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC) :4735-4740

[5] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Moriel, Patricia ;

Amar, Fernando ;

Valdes, Carlos .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4792-4795

[6] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].

Barluenga, José ;

Moriel, Patricia ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590

[7] Synthesis of Polysubstituted Olefins by Pd-Catalyzed Cross-Coupling Reaction of Tosylhydrazones and Aryl Nonaflates [J].

Barluenga, Jose ;

Florentino, Lucia ;

Aznar, Fernando ;

Valdes, Carlos .

ORGANIC LETTERS, 2011, 13 (03) :510-513

[8] Synthesis of Dienes by Palladium-Catalyzed Couplings of Tosylhydrazones with Aryl and Alkenyl Halides [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Aznar, Fernando ;

Valdes, Carlos .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3235-3240

[9] Pd-Catalyzed Autotandem C-C/C-C Bond-Forming Reactions with Tosylhydrazones: Synthesis of Spirocycles with Extended π-Conjugation [J].

Barroso, Raquel ;

Valencia, Rocio A. ;

Cabal, Maria-Paz ;

Valdes, Carlos .

ORGANIC LETTERS, 2014, 16 (08) :2264-2267

[10] One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles [J].

Bzeih, Tourin ;

Zhang, Kena ;

Khalaf, Ali ;

Hachem, Ali ;

Alami, Mouad ;

Hamze, Abdallah .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (01) :228-238

← 1 2 3 4 5 →