Literature DB >> 20088536

Rapid decarboxylative allylation of nitroalkanes.

Alexander J Grenning1, Jon A Tunge.   

Abstract

Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because O-allylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.

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Year:  2010        PMID: 20088536      PMCID: PMC2821453          DOI: 10.1021/ol902828p

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


  5 in total

1.  Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

Authors:  Erin C Burger; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2006-08-09       Impact factor: 15.419

2.  Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

Authors:  Shelli R Waetzig; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2007-11-08       Impact factor: 15.419

3.  Decarboxylative allylation using sulfones as surrogates of alkanes.

Authors:  Jimmie D Weaver; Jon A Tunge
Journal:  Org Lett       Date:  2008-09-12       Impact factor: 6.005

Review 4.  Asymmetric synthesis of tertiary alcohols and alpha-tertiary amines via Cu-catalyzed C-C bond formation to ketones and ketimines.

Authors:  Masakatsu Shibasaki; Motomu Kanai
Journal:  Chem Rev       Date:  2008-06-21       Impact factor: 60.622

5.  C-C bond-forming reactions via Pd-mediated decarboxylative alpha-imino anion generation.

Authors:  Andrew A Yeagley; Jason J Chruma
Journal:  Org Lett       Date:  2007-06-20       Impact factor: 6.005

  5 in total
  11 in total

1.  Mechanistic origin of the stereodivergence in decarboxylative allylation.

Authors:  Kalicharan Chattopadhyay; Ranjan Jana; Victor W Day; Justin T Douglas; Jon A Tunge
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

Review 3.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

4.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

5.  Nitroethylation of vinyl triflates and bromides.

Authors:  Rosaura Padilla-Salinas; Ryan R Walvoord; Sergei Tcyrulnikov; Marisa C Kozlowski
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

6.  Migratory decarboxylative coupling of coumarins: synthetic and mechanistic aspects.

Authors:  Ranjan Jana; James J Partridge; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

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.  2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids.

Authors:  Alison E Metz; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-01-02       Impact factor: 4.354

9.  Intercepted Decarboxylative Allylations of Nitroalkanoates.

Authors:  Meghan Schmitt; Alexander J Grenning; Jon A Tunge
Journal:  Tetrahedron Lett       Date:  2012-06-07       Impact factor: 2.415

10.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

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