Literature DB >> 29474078

Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols.

Hong Zhang1, Paula Ruiz-Castillo1, Stephen L Buchwald1.   

Abstract

Two catalyst systems are described, which together provide mild and general conditions for the Pd-catalyzed C-O cross-coupling of primary alcohols. For activated substrates, such as electron-deficient aryl halides, the commercially available ligand L2 promotes efficient coupling for a variety of alcohol nucleophiles. In the case of unactivated electrophiles, such as electron-rich aryl halides, the new ligand L8 was developed to improve these challenging C-O bond-forming reactions.

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Year:  2018        PMID: 29474078      PMCID: PMC5856650          DOI: 10.1021/acs.orglett.8b00325

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


  26 in total

1.  Mitsunobu and related reactions: advances and applications.

Authors:  K C Kumara Swamy; N N Bhuvan Kumar; E Balaraman; K V P Pavan Kumar
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

2.  A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols.

Authors:  Saravanan Gowrisankar; Alexey G Sergeev; Pazhamalai Anbarasan; Anke Spannenberg; Helfried Neumann; Matthias Beller
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

3.  C-O cross-coupling of activated aryl and heteroaryl halides with aliphatic alcohols.

Authors:  Peter E Maligres; Jing Li; Shane W Krska; John D Schreier; Izzat T Raheem
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

4.  Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.

Authors:  Andrei V Vorogushin; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-06-08       Impact factor: 15.419

5.  Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics.

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Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

6.  Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts.

Authors:  Sunil K Sundalam; David R Stuart
Journal:  J Org Chem       Date:  2015-06-09       Impact factor: 4.354

7.  Alkyl Aryl Ether Bond Formation with PhenoFluor.

Authors:  Xiao Shen; Constanze N Neumann; Claudia Kleinlein; Nathaniel W Goldberg; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-20       Impact factor: 15.336

8.  Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.

Authors:  Martina Wolter; Gero Nordmann; Gabriel E Job; Stephen L Buchwald
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

9.  Diaryliodonium salts: a journey from obscurity to fame.

Authors:  Eleanor A Merritt; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

Authors:  Ryan A Altman; Alexandr Shafir; Alice Choi; Phillip A Lichtor; Stephen L Buchwald
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354

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  14 in total

1.  Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.

Authors:  Jessica Xu; Richard Y Liu; Charles S Yeung; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-06-21       Impact factor: 13.084

2.  Improved Process for the Palladium-Catalyzed C-O Cross-Coupling of Secondary Alcohols.

Authors:  Hong Zhang; Paula Ruiz-Castillo; Alexander W Schuppe; Stephen L Buchwald
Journal:  Org Lett       Date:  2020-06-24       Impact factor: 6.005

3.  Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.

Authors:  Sergei Tcyrulnikov; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2020-02-12       Impact factor: 4.354

4.  Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

Authors:  Mixiang Tian; Lidong Shao; Xiaosan Su; Xuhong Zhou; Honglei Zhang; Kun Wei; Ruifen Sun; Junliang Wang
Journal:  RSC Adv       Date:  2022-06-27       Impact factor: 4.036

5.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

6.  Oxalohydrazide Ligands for Copper-Catalyzed C-O Coupling Reactions with High Turnover Numbers.

Authors:  Ritwika Ray; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

7.  Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides.

Authors:  Cristian Cavedon; Amiera Madani; Peter H Seeberger; Bartholomäus Pieber
Journal:  Org Lett       Date:  2019-06-24       Impact factor: 6.005

8.  Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.

Authors:  Hai-Jun Zhang; Longrui Chen; Martins S Oderinde; Jacob T Edwards; Yu Kawamata; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-15       Impact factor: 16.823

9.  Dialkyl Ether Formation at High-Valent Nickel.

Authors:  Franck Le Vaillant; Edward J Reijerse; Markus Leutzsch; Josep Cornella
Journal:  J Am Chem Soc       Date:  2020-11-03       Impact factor: 15.419

10.  Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling.

Authors:  Robert Szpera; Patrick G Isenegger; Maxime Ghosez; Natan J W Straathof; Rosa Cookson; David C Blakemore; Paul Richardson; Véronique Gouverneur
Journal:  Org Lett       Date:  2020-08-04       Impact factor: 6.005

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