Literature DB >> 22390789

Suzuki coupling of potassium cyclopropyl- and alkoxymethyltrifluoroborates with benzyl chlorides.

Virginie Colombel1, Frederik Rombouts, Daniel Oehlrich, Gary A Molander.   

Abstract

Efficient Csp(3)-Csp(3) Suzuki couplings have been developed with both potassium cyclopropyl- and alkoxymethyltrifluoroborates. Moderate to good yields have been achieved in the cross-coupling of potassium cyclopropyltrifluoroborate with benzyl chlorides possessing electron-donating or electron-withdrawing substituents. Benzyl chloride was also successfully cross-coupled to potassium alkoxymethyltrifluoroborates derived from primary, secondary, and tertiary alcohols.

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Year:  2012        PMID: 22390789      PMCID: PMC3306449          DOI: 10.1021/jo202686p

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


  25 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling.

Authors:  Masahiro Miura
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

3.  PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS-COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM-TEMPERATURE: (13-CHLOROTRIDECYLOXY)TRIETHYLSILANE [Silane, [(13-chlorotridecyl)oxy]triethyl-].

Authors:  Sha Lou; Gregory C Fu; Takuyo Higo; Tohru Fukuyama
Journal:  Organic Synth       Date:  2010-01-01

4.  Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors:  M R Netherton; C Dai; K Neuschütz; G C Fu
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

5.  Silver Oxide Mediated Palladium-Catalyzed Cross-Coupling Reaction of Cyclopropylboronic Acids with Allylic Bromides.

Authors: 
Journal:  J Org Chem       Date:  2000-07-14       Impact factor: 4.354

6.  Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Authors:  Gary A Molander; Maxwell D Elia
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

7.  Pd-catalyzed cross-coupling reactions of alkyl halides.

Authors:  Nobuaki Kambe; Takanori Iwasaki; Jun Terao
Journal:  Chem Soc Rev       Date:  2011-07-25       Impact factor: 54.564

8.  High yielding alkylations of unactivated sp3 and sp2 centres with alkyl-9-BBN reagents using an NHC-based catalyst: Pd-PEPPSI-IPrf.

Authors:  Cory Valente; Sylvia Baglione; David Candito; Christopher J O'Brien; Michael G Organ
Journal:  Chem Commun (Camb)       Date:  2008-02-14       Impact factor: 6.222

9.  N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors:  Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

10.  Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Org Lett       Date:  2008-04-26       Impact factor: 6.005

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  2 in total

1.  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

2.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

  2 in total

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