Literature DB >> 23885976

Nitroethylation of vinyl triflates and bromides.

Rosaura Padilla-Salinas1, Ryan R Walvoord, Sergei Tcyrulnikov, Marisa C Kozlowski.   

Abstract

A two-carbon homologation of vinyl triflates and bromides for the synthesis of homoallylic nitro products is described. This palladium-catalyzed double coupling of nitromethane exploits the anion stabilizing and leaving group properties of nitromethane, generating the homo allyl nitro products via a tandem cross-coupling/π-allylation sequence. The resultant process provides a mild and convenient entry to nitroethylated products, which are versatile precursors to β,γ-unsaturated carbonyls, homoallylic amines, and nitrile oxides.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23885976      PMCID： PMC3775651          DOI： 10.1021/ol401747u

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


  13 in total

1.  Asymmetric Alkylation of Nitroalkanes We thank the National Science Foundation and the National Institutes of Health (NIH), General Medical Sciences, for their generous support of our programs. Rhône-Poulenc graciously provided a postdoctoral fellowship for J.-P. S. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

Review 2.  Concurrent tandem catalysis.

Authors:  Julia-Christina Wasilke; Stephen J Obrey; R Tom Baker; Guillermo C Bazan
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

3.  Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones.

Authors:  Barry M Trost; Lara C Czabaniuk
Journal:  J Am Chem Soc       Date:  2012-03-22       Impact factor: 15.419

4.  A new pathway for hydroamination. Mechanism of palladium-catalyzed addition of anilines to vinylarenes.

Authors:  Ulrike Nettekoven; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

5.  pi-Allylic C1-substitution in water with nitromethane using amphiphilic resin-supported palladium complexes.

Authors:  Yasuhiro Uozumi; Toshimasa Suzuka
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

6.  Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles.

Authors:  Barry M Trost; Lara C Czabaniuk
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

7.  Deacylative allylation of nitroalkanes: unsymmetric bisallylation by a three-component coupling.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

8.  Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters.

Authors:  Ryoichi Kuwano; Yutaka Kondo; Yosuke Matsuyama
Journal:  J Am Chem Soc       Date:  2003-10-08       Impact factor: 15.419

9.  Rapid decarboxylative allylation of nitroalkanes.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

10.  Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent.

Authors:  Ryan R Walvoord; Simon Berritt; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-07-27       Impact factor: 6.005
View more
  4 in total

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

Authors:  Xiaodong Yang; Byeong-Seon Kim; Minyan Li; Patrick J Walsh
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides.

Authors:  Sina Rezazadeh; Vijayarajan Devannah; Donald A Watson
Journal:  J Am Chem Soc       Date:  2017-06-08       Impact factor: 15.419

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.  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
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.