Literature DB >> 23131122

Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

Nicolas Fleury-Brégeot1, Marc Presset, Floriane Beaumard, Virginie Colombel, Daniel Oehlrich, Frederik Rombouts, Gary A Molander.   

Abstract

The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.

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Year:  2012        PMID: 23131122      PMCID: PMC3514869          DOI: 10.1021/jo3021665

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  27 in total

1.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

2.  New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors:  Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

Review 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

Review 5.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

6.  Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

7.  Copper(I)-catalyzed boryl substitution of unactivated alkyl halides.

Authors:  Hajime Ito; Koji Kubota
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

8.  Aryl trifluoroborates in Suzuki-Miyaura coupling: the roles of endogenous aryl boronic acid and fluoride.

Authors:  Mike Butters; Jeremy N Harvey; Jesus Jover; Alastair J J Lennox; Guy C Lloyd-Jones; Paul M Murray
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-12       Impact factor: 15.336

9.  Organotrifluoroborate hydrolysis: boronic acid release mechanism and an acid-base paradox in cross-coupling.

Authors:  Alastair J J Lennox; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2012-04-19       Impact factor: 15.419

10.  Functional group tolerant Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents.

Authors:  Oleg Vechorkin; Valérie Proust; Xile Hu
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419

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  9 in total

1.  Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Authors:  Daniel A Everson; Joseph A Buonomo; Daniel J Weix
Journal:  Synlett       Date:  2014-01       Impact factor: 2.454

2.  Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

3.  Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine.

Authors:  Beau P Pritchett; Jun Kikuchi; Yoshitaka Numajiri; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-26       Impact factor: 15.336

4.  Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate.

Authors:  Daniel A Everson; David T George; Daniel J Weix; Jonas F Buergler; John L Wood
Journal:  Organic Synth       Date:  2013

5.  Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides.

Authors:  Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-14       Impact factor: 6.005

6.  Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors:  Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-04-17       Impact factor: 4.354

7.  Carbonylative Suzuki couplings of aryl bromides with boronic acid derivatives under base-free conditions.

Authors:  Klaus M Bjerglund; Troels Skrydstrup; Gary A Molander
Journal:  Org Lett       Date:  2014-03-17       Impact factor: 6.005

8.  Facile formation of β-hydroxyboronate esters by a Cu-catalyzed diboration/Matteson homologation sequence.

Authors:  Cameron M Moore; Casey R Medina; Peter C Cannamela; Melissa L McIntosh; Carl J Ferber; Andrew J Roering; Timothy B Clark
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005

9.  Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Org Lett       Date:  2016-08-18       Impact factor: 6.005

  9 in total

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