Literature DB >> 23489071

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

Nicolas Fleury-Brégeot1, Daniel Oehlrich, Frederik Rombouts, Gary A Molander.   

Abstract

A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides the key organotrifluoroborate reagent.

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Year:  2013        PMID： 23489071      PMCID： PMC3663905          DOI： 10.1021/ol400320q

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


  15 in total

1.  Double arylation of allyl alcohol via a one-pot Heck arylation-isomerization-acylation cascade.

Authors:  Paul Colbon; Jiwu Ruan; Mark Purdie; Keith Mulholland; Jianliang Xiao
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

2.  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

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

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

5.  Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-Plus couplings.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

6.  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

7.  Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction.

Authors:  R A Bunce; D M Herron; L B Johnson; S V Kotturi
Journal:  J Org Chem       Date:  2001-04-20       Impact factor: 4.354

8.  Stereospecific Suzuki cross-coupling of alkyl alpha-cyanohydrin triflates.

Authors:  Anyu He; J R Falck
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

9.  Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

Authors:  Arkady Krasovskiy; Christophe Duplais; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

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

Authors:  Nicolas Fleury-Brégeot; Marc Presset; Floriane Beaumard; Virginie Colombel; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2012-11-06       Impact factor: 4.354
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  1 in total

1.  Synthesis, biological evaluation and molecular modelling of 2,4-disubstituted-5-(6-alkylpyridin-2-yl)-1H-imidazoles as ALK5 inhibitors.

Authors:  Myoung-Soon Park; Hyun-Ju Park; Young Jae An; Joon Hun Choi; Geunyoung Cha; Hwa Jeong Lee; So-Jung Park; Purushottam M Dewang; Dae-Kee Kim
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051
  1 in total

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