Literature DB >> 11700143

Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides.

M Wolter1, A Klapars, S L Buchwald.   

Abstract

[reaction--see text] A convenient method for intermolecular N-arylation of hydrazides with substituted aryl iodides in the presence of a copper catalyst and Cs(2)CO(3) is reported. The C-N coupling of N-Boc hydrazine with para- and meta-substituted aryl iodides afforded the N-arylated products A, regioselectively. A reversal in regioselectivity is observed for the arylation of benzoic hydrazide with ortho-substituted aryl iodides, providing the N'-arylated products B.

Entities:  

Mesh：

Substances：

Year:  2001        PMID： 11700143     DOI： 10.1021/ol0168216

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold.

Authors:  Claudio Martínez; Michele Lieb; Susana Alvarez; Fátima Rodríguez-Barrios; Rosana Alvarez; Harshal Khanwalkar; Hinrich Gronemeyer; Angel R de Lera
Journal:  ACS Med Chem Lett       Date:  2014-03-19       Impact factor: 4.345

2.  Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions.

Authors:  Peter D Johnson; Jeong-Hun Sohn; Viresh H Rawal
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

3.  Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides.

Authors:  Hao Wang; Hoimin Jung; Fangfang Song; Shiyang Zhu; Ziqian Bai; Danye Chen; Gang He; Sukbok Chang; Gong Chen
Journal:  Nat Chem       Date:  2021-03-22       Impact factor: 24.427

4.  Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols.

Authors:  Debabrata Maiti; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

5.  A Modular Approach to Arylazo-1,2,3-triazole Photoswitches.

Authors:  Jeremy R Tuck; Robert J Tombari; Noah Yardeny; David E Olson
Journal:  Org Lett       Date:  2021-05-21       Impact factor: 6.072

6.  Synthesis, characterisation and reactivity of copper(I) amide complexes and studies on their role in the modified Ullmann amination reaction.

Authors:  Simon Sung; D Christopher Braddock; Alan Armstrong; Colin Brennan; David Sale; Andrew J P White; Robert P Davies
Journal:  Chemistry       Date:  2015-03-18       Impact factor: 5.236

7.  Origins of high catalyst loading in copper(i)-catalysed Ullmann-Goldberg C-N coupling reactions.

Authors:  Grant J Sherborne; Sven Adomeit; Robert Menzel; Jabor Rabeah; Angelika Brückner; Mark R Fielding; Charlotte E Willans; Bao N Nguyen
Journal:  Chem Sci       Date:  2017-08-29       Impact factor: 9.825

8.  New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for Green C-N Coupling: Synthesis of N-(Pyridin-4-yl)benzene Amines and N,N-Bis(pyridine-4-yl)benzene Amines.

Authors:  Nitin Kore; Pavel Pazdera
Journal:  Molecules       Date:  2016-12-22       Impact factor: 4.411

9.  New efficient ligand for sub-mol % copper-catalyzed C-N cross-coupling reactions running under air.

Authors:  Per-Fredrik Larsson; Peter Astvik; Per-Ola Norrby
Journal:  Beilstein J Org Chem       Date:  2012-11-09       Impact factor: 2.883

10.  Starazo triple switches - synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes.

Authors:  Andreas H Heindl; Hermann A Wegner
Journal:  Beilstein J Org Chem       Date:  2020-01-03       Impact factor: 2.883
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.