Literature DB >> 14507200

Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Lei Jiang1, Gabriel E Job, Artis Klapars, Stephen L Buchwald.   

Abstract

[reaction: see text] A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N'-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

Entities:  

Mesh:

Substances:

Year:  2003        PMID: 14507200     DOI: 10.1021/ol035355c

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


  38 in total

1.  Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

Authors:  M Shahjahan Kabir; Ojas A Namjoshi; Ranjit Verma; Michael Lorenz; V V N Phani Babu Tiruveedhula; Aaron Monte; Steven H Bertz; Alan W Schwabacher; James M Cook
Journal:  J Org Chem       Date:  2011-11-28       Impact factor: 4.354

2.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

3.  Toward the synthesis of cobyric acid. Enantioselective syntheses of completely differentiated ring D synthons.

Authors:  Hui Wang; Carlos Tassa; Peter A Jacobi
Journal:  Org Lett       Date:  2008-06-07       Impact factor: 6.005

4.  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

5.  Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Authors:  Rodolfo Tello-Aburto; Emily M Johnson; Cheyenne K Valdez; William A Maio
Journal:  Org Lett       Date:  2012-04-04       Impact factor: 6.005

6.  Mechanistic studies on the copper-catalyzed N-arylation of amides.

Authors:  Eric R Strieter; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

7.  Synthetic libraries of tyrosine-derived bacterial metabolites.

Authors:  Savvas N Georgiades; Jon Clardy
Journal:  Bioorg Med Chem Lett       Date:  2007-10-22       Impact factor: 2.823

8.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

9.  Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Authors:  Panduka B Koswatta; Jayanta Das; Muhammed Yousufuddin; Carl J Lovely
Journal:  European J Org Chem       Date:  2015-04

10.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.