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Literature DB >> 19663467

A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

Brijesh Bhayana¹, Brett P Fors, Stephen L Buchwald.

Abstract

A catalyst system for the Suzuki-Miyaura cross-coupling reactions of n class="Chemical">aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids with aryl tosylates and mesylates to be performed in high yields. Moreover, reactions employing alkylboronic acids, as well as heteroaryl, vinyl, and allylic pinacol boronate esters, were conducted with high efficiencies.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19663467 PMCID： PMC2759755 DOI： 10.1021/ol9015892

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

23 in total

Review 1. Selected patented cross-coupling reaction technologies.

Authors: Jean-Pierre Corbet; Gérard Mignani
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

2. A general palladium-catalyzed Suzuki-Miyaura coupling of aryl mesylates.

Authors: Chau Ming So; Chak Po Lau; Fuk Yee Kwong
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

4. Preparation of enamides via palladium-catalyzed amidation of enol tosylates.

Authors: Artis Klapars; Kevin R Campos; Cheng-Yi Chen; Ralph P Volante
Journal: Org Lett Date: 2005-03-17 Impact factor: 6.005

5. A new synthesis of butadienyl- and styrylboronic esters: highly reactive intermediates for Suzuki cross-coupling.

Authors: Paolo Balma Tivola; Annamaria Deagostino; Cristina Prandi; Paolo Venturello
Journal: Org Lett Date: 2002-04-18 Impact factor: 6.005

6. Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

Authors: David X Yang; Steven L Colletti; Kevin Wu; Maoying Song; George Y Li; Hong C Shen
Journal: Org Lett Date: 2009-01-15 Impact factor: 6.005

7. Two-step, one-pot Ni-catalyzed neopentylglycolborylation and complementary Pd/Ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates.

Authors: Daniela A Wilson; Christopher J Wilson; Brad M Rosen; Virgil Percec
Journal: Org Lett Date: 2008-09-26 Impact factor: 6.005

8. Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts.

Authors: Chau Ming So; Chak Po Lau; Albert S C Chan; Fuk Yee Kwong
Journal: J Org Chem Date: 2008-09-11 Impact factor: 4.354

9. Palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates.

Authors: Liang Zhang; Tianhao Meng; Jie Wu
Journal: J Org Chem Date: 2007-11-02 Impact factor: 4.354

10. Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

Authors: Nicolas Marion; Oscar Navarro; Jianguo Mei; Edwin D Stevens; Natalie M Scott; Steven P Nolan
Journal: J Am Chem Soc Date: 2006-03-29 Impact factor: 15.419

19 in total

1. Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors: Scott E Denmark; Christopher S Regens
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

Review 2. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors: Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal: Chem Rev Date: 2010-12-06 Impact factor: 60.622

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. Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate.

Authors: Gary A Molander; Floriane Beaumard; Terren K Niethamer
Journal: J Org Chem Date: 2011-09-02 Impact factor: 4.354

5. Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates.

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

6. Activity of Fluorine-Containing Analogues of WC-9 and Structurally Related Analogues against Two Intracellular Parasites: Trypanosoma cruzi and Toxoplasma gondii.

Authors: María N Chao; Catherine Li; Melissa Storey; Bruno N Falcone; Sergio H Szajnman; Sergio M Bonesi; Roberto Docampo; Silvia N J Moreno; Juan B Rodriguez
Journal: ChemMedChem Date: 2016-11-25 Impact factor: 3.466

7. Aryloxyethyl Thiocyanates Are Potent Growth Inhibitors of Trypanosoma cruzi and Toxoplasma gondii.

Authors: María N Chao; Carolina Exeni Matiuzzi; Melissa Storey; Catherine Li; Sergio H Szajnman; Roberto Docampo; Silvia N J Moreno; Juan B Rodriguez
Journal: ChemMedChem Date: 2015-04-27 Impact factor: 3.466

8. Design, synthesis and biological evaluation of WC-9 analogs as antiparasitic agents.

Authors: Pablo D Elicio; María N Chao; Melina Galizzi; Catherine Li; Sergio H Szajnman; Roberto Docampo; Silvia N J Moreno; Juan B Rodriguez
Journal: Eur J Med Chem Date: 2013-09-18 Impact factor: 6.514

9. Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

Authors: Masayuki Wasa; Brady T Worrell; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2010-02-08 Impact factor: 15.336

10. Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors: Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal: ACS Catal Date: 2018-09-20 Impact factor: 13.084