Literature DB >> 27160421

Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

Xiaodong Yang1,2, Byeong-Seon Kim2, Minyan Li2, Patrick J Walsh2.   

Abstract

An efficient palladium-catalyzed α-alkenylation of pyridylmethyl ethers with vinyl bromides is presented. A Pd/NIXANTPHOS-based catalyst system enables a mild and chemoselective coupling between a variety of pyridylmethyl ethers and vinyl bromides in good to excellent yields. Under the mild conditions, β,γ-unsaturated products are obtained without isomerization or Heck byproducts observed.

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Year:  2016        PMID： 27160421      PMCID： PMC4887130          DOI： 10.1021/acs.orglett.6b00815

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


  26 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Single-Flask Multicomponent Palladium-Catalyzed α,γ-Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds.

Authors:  Michael Grigalunas; Per-Ola Norrby; Olaf Wiest; Paul Helquist
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-14       Impact factor: 15.336

3.  Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes.

Authors:  Fabiola Barrios-Landeros; Brad P Carrow; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

4.  Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

Authors:  Jiadi Zhang; Ana Bellomo; Andrea D Creamer; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

5.  Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation.

Authors:  Leo A Hardegger; Jacqueline Habegger; Timothy J Donohoe
Journal:  Org Lett       Date:  2015-06-18       Impact factor: 6.005

6.  Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

Authors:  Byeong-Seon Kim; Jacqueline Jiménez; Feng Gao; Patrick J Walsh
Journal:  Org Lett       Date:  2015-11-17       Impact factor: 6.005

7.  Palladium- (and nickel-) catalyzed vinylation of aryl halides.

Authors:  Scott E Denmark; Christopher R Butler
Journal:  Chem Commun (Camb)       Date:  2008-08-27       Impact factor: 6.222

8.  Palladium-catalyzed alpha-vinylation of carbonyl compounds.

Authors:  Jinkun Huang; Emilio Bunel; Margaret M Faul
Journal:  Org Lett       Date:  2007-09-22       Impact factor: 6.005

9.  Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.

Authors:  Alexandra R Rivero; Byeong-Seon Kim; Patrick J Walsh
Journal:  Org Lett       Date:  2016-03-23       Impact factor: 6.005

10.  Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Commun (Camb)       Date:  2014-07-31       Impact factor: 6.222
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  9 in total

1.  Palladium-Catalyzed Triarylation of sp3 C-H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes.

Authors:  Shuguang Zhang; Bowen Hu; Zhipeng Zheng; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2018-02-03       Impact factor: 5.837

2.  Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst.

Authors:  Gui Gao; Yue Fu; Minyan Li; Bo Wang; Bing Zheng; Shicong Hou; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2017-07-12       Impact factor: 5.837

3.  Transition-metal-free chemo- and regioselective vinylation of azaallyls.

Authors:  Minyan Li; Osvaldo Gutierrez; Simon Berritt; Ana Pascual-Escudero; Ahmet Yeşilçimen; Xiaodong Yang; Javier Adrio; Georgia Huang; Eiko Nakamaru-Ogiso; Marisa C Kozlowski; Patrick J Walsh
Journal:  Nat Chem       Date:  2017-04-17       Impact factor: 24.427

4.  Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.

Authors:  Minyan Li; Simon Berritt; Lucas Matuszewski; Guogang Deng; Ana Pascual-Escudero; Grace B Panetti; Michal Poznik; Xiaodong Yang; Jason J Chruma; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2017-10-31       Impact factor: 15.419

5.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336

6.  Palladium-catalysed synthesis of triaryl(heteroaryl)methanes.

Authors:  Shuguang Zhang; Byeong-Seon Kim; Chen Wu; Jianyou Mao; Patrick J Walsh
Journal:  Nat Commun       Date:  2017-03-14       Impact factor: 14.919

7.  Biointeractions of Herbicide Atrazine with Human Serum Albumin: UV-Vis, Fluorescence and Circular Dichroism Approaches.

Authors:  Meiqing Zhu; Lijun Wang; Yu Wang; Jie Zhou; Jie Ding; Wei Li; Yue Xin; Shisuo Fan; Zhen Wang; Yi Wang
Journal:  Int J Environ Res Public Health       Date:  2018-01-11       Impact factor: 3.390

Review 8.  Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.

Authors:  Ugo Azzena; Massimo Carraro; Luisa Pisano; Serena Monticelli; Roberta Bartolotta; Vittorio Pace
Journal:  ChemSusChem       Date:  2018-11-20       Impact factor: 8.928

9.  Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.

Authors:  Haoqiang Zhao; Xin Xu; Zhenli Luo; Lei Cao; Bohan Li; Huanrong Li; Lijin Xu; Qinghua Fan; Patrick J Walsh
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825
  9 in total

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