Literature DB >> 19827762

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

Arkady Krasovskiy1, Christophe Duplais, Bruce H Lipshutz.   

Abstract

Mix in water, stir. That is all that is required in this new approach to sp(3)-sp(2) cross-couplings between an alkyl iodide and an aryl bromide, both potentially bearing functionality. They react under catalysis by Pd(0) in the presence of zinc powder, aided by a nonionic amphiphile, to give the alkylated aromatic. No organic solvents and no heating; just add water.

Entities:  

Year:  2009        PMID： 19827762      PMCID： PMC3359135          DOI： 10.1021/ja906803t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  "On water": unique reactivity of organic compounds in aqueous suspension.

Authors:  Sridhar Narayan; John Muldoon; M G Finn; Valery V Fokin; Hartmuth C Kolb; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-20       Impact factor: 15.336

2.  Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update.

Authors:  Chao-Jun Li
Journal:  Chem Rev       Date:  2005-08       Impact factor: 60.622

3.  Domino iron catalysis: direct aryl-alkyl cross-coupling.

Authors:  Waldemar Maximilian Czaplik; Matthias Mayer; Axel Jacobi von Wangelin
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Bis(mu-oxo)dicopper(III) complexes of a homologous series of simple peralkylated 1,2-diamines: steric modulation of structure, stability, and reactivity.

Authors:  Adam P Cole; Viswanath Mahadevan; Liviu M Mirica; Xavier Ottenwaelder; T Daniel P Stack
Journal:  Inorg Chem       Date:  2005-10-17       Impact factor: 5.165

5.  On the mechanism of palladium-catalyzed coupling of haloaryls to biaryls in water with zinc

Authors: 
Journal:  Org Lett       Date:  2000-01-27       Impact factor: 6.005

6.  Activation of organozinc reagents with t-Bu-P4 base for transition metal-free catalytic SN2' reaction.

Authors:  Koji Kobayashi; Masahiro Ueno; Hiroshi Naka; Yoshinori Kondo
Journal:  Chem Commun (Camb)       Date:  2008-06-20       Impact factor: 6.222

7.  Effective Pd-nanoparticle (PdNP)-catalyzed Negishi coupling involving alkylzinc reagents at room temperature.

Authors:  Jing Liu; Yi Deng; Haibo Wang; Hua Zhang; Ganxiang Yu; Bingbin Wu; Heng Zhang; Qiang Li; Todd B Marder; Zhen Yang; Aiwen Lei
Journal:  Org Lett       Date:  2008-05-29       Impact factor: 6.005

8.  Alkenenitriles: conjugate additions of alkyl iodides with a silica-supported zinc-copper matrix in water.

Authors:  Fraser F Fleming; Subrahmanyam Gudipati; Jennifer A Aitken
Journal:  J Org Chem       Date:  2007-08-08       Impact factor: 4.354
  8 in total
  43 in total

1.  Metallaphotoredox-Catalyzed Cross-Electrophile Csp3-Csp3 Coupling of Aliphatic Bromides.

Authors:  Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

Review 3.  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

4.  Kinetically guided radical-based synthesis of C(sp3)-C(sp3) linkages on DNA.

Authors:  Jie Wang; Helena Lundberg; Shota Asai; Pedro Martín-Acosta; Jason S Chen; Stephen Brown; William Farrell; Russell G Dushin; Christopher J O'Donnell; Anokha S Ratnayake; Paul Richardson; Zhiqing Liu; Tian Qin; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2018-06-26       Impact factor: 11.205

5.  Ligand effects on Negishi couplings of alkenyl halides.

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

6.  "On water" sp3-sp2 cross-couplings between benzylic and alkenyl halides.

Authors:  Valeria Krasovskaya; Arkady Krasovskiy; Anish Bhattacharjya; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2011-04-12       Impact factor: 6.222

7.  Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

Authors:  Stefan R K Minkler; Nicholas A Isley; Daniel J Lippincott; Norbert Krause; Bruce H Lipshutz
Journal:  Org Lett       Date:  2014-01-16       Impact factor: 6.005

8.  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

9.  Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

Authors:  Christophe Duplais; Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Organometallics       Date:  2011-11-21       Impact factor: 3.876

10.  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
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