Literature DB >> 21913292

A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols.

Xiaoxing Wu1, Brett P Fors, Stephen L Buchwald.   

Abstract

Forging a bond: an efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21913292      PMCID: PMC3465471          DOI: 10.1002/anie.201104361

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  20 in total

1.  An efficient intermolecular palladium-catalyzed synthesis of aryl ethers.

Authors:  K E Torraca; X Huang; C A Parrish; S L Buchwald
Journal:  J Am Chem Soc       Date:  2001-10-31       Impact factor: 15.419

2.  Palladium-catalyzed intramolecular C-O bond formation.

Authors:  S I Kuwabe; K E Torraca; S L Buchwald
Journal:  J Am Chem Soc       Date:  2001-12-12       Impact factor: 15.419

3.  Palladium-catalyzed formation of aryl tert-butyl ethers from unactivated aryl halides.

Authors:  C A Parrish; S L Buchwald
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

4.  A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.

Authors:  Brett P Fors; Donald A Watson; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

5.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.

Authors:  Takashi Ikawa; Timothy E Barder; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

6.  Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.

Authors:  Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

7.  Copper(I)-catalyzed aryl bromides to form intermolecular and intramolecular carbon-oxygen bonds.

Authors:  Jiajia Niu; Pengran Guo; Juntao Kang; Zhigang Li; Jingwei Xu; Shaojing Hu
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

8.  Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.

Authors:  Donald A Watson; Mingjuan Su; Georgiy Teverovskiy; Yong Zhang; Jorge García-Fortanet; Tom Kinzel; Stephen L Buchwald
Journal:  Science       Date:  2009-08-13       Impact factor: 47.728

9.  General, mild, and intermolecular Ullmann-type synthesis of diaryl and alkyl aryl ethers catalyzed by diol-copper(I) complex.

Authors:  Ajay B Naidu; E A Jaseer; Govindasamy Sekar
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

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

View more
  24 in total

1.  Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C-H Functionalization.

Authors:  Landon J Durak; James T Payne; Jared C Lewis
Journal:  ACS Catal       Date:  2016-01-25       Impact factor: 13.084

2.  Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Authors:  Nathaniel H Park; Ekaterina V Vinogradova; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

3.  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

4.  A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions.

Authors:  Luca Salvi; Nicole R Davis; Siraj Z Ali; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-12-19       Impact factor: 6.005

5.  Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.

Authors:  Seo-Jung Han; Ryohei Doi; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

6.  Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.

Authors:  Bryan T Ingoglia; Stephen L Buchwald
Journal:  Org Lett       Date:  2017-05-12       Impact factor: 6.005

7.  Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-24       Impact factor: 6.005

8.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

9.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

10.  Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

Authors:  Nicholas C Bruno; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-05-15       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.