Literature DB >> 11843607

Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine.

Artyom Y Lebedev1, Vyatcheslav V Izmer, Denis N Kazyul'kin, Irina P Beletskaya, Alexander Z Voskoboynikov.   

Abstract

[reaction: see text] Vinylation of various azoles (pyrrole, indole, carbazole, and their derivatives) and phenothiazine with vinyl bromides catalyzed by palladium-phosphine complexes results in the respective N-vinylazoles in 30-99% yields. This reaction with cis- and trans-beta-bromostyrenes is stereospecific giving the respective products with full retention of configuration.

Entities:  

Year:  2002        PMID： 11843607     DOI： 10.1021/ol0172370

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


  13 in total

1.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Dimerization of (+)-Myrmicarin 215B. A Potential Biomimetic Approach to Complex Myrmicarin Alkaloids.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Tetrahedron       Date:  2006-05-29       Impact factor: 2.457

3.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

5.  Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

Review 6.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Synthetic studies of roquefortine C: synthesis of isoroquefortine C and a heterocycle.

Authors:  David J Richard; Bruno Schiavi; Madeleine M Joullié
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-12       Impact factor: 11.205

8.  Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.

Authors:  Matthew P Rainka; Yimon Aye; Stephen L Buchwald
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

9.  Total synthesis and study of myrmicarin alkaloids.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Chem Commun (Camb)       Date:  2009-05-19       Impact factor: 6.222

10.  Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides.

Authors:  Joshua R Dunetz; Rick L Danheiser
Journal:  Org Lett       Date:  2003-10-16       Impact factor: 6.005
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