Literature DB >> 14535766

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

Joshua R Dunetz1, Rick L Danheiser.   

Abstract

[reaction: see text] A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.

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Year:  2003        PMID： 14535766      PMCID： PMC2897059          DOI： 10.1021/ol035647d

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


  17 in total

1.  Organic Polyvalent Iodine Compounds.

Authors:  Peter J. Stang; Viktor V. Zhdankin
Journal:  Chem Rev       Date:  1996-05-09       Impact factor: 60.622

2.  A highly efficient and flexible synthesis of substituted carbazoles by rhodium-catalyzed inter- and intramolecular alkyne cyclotrimerizations.

Authors:  Bernhard Witulski; Carole Alayrac
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-02       Impact factor: 15.336

Review 3.  Recent developments in the chemistry of polyvalent iodine compounds.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2002-07       Impact factor: 60.622

4.  Rhodium(I)-Catalyzed

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

5.  Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine.

Authors:  Artyom Y Lebedev; Vyatcheslav V Izmer; Denis N Kazyul'kin; Irina P Beletskaya; Alexander Z Voskoboynikov
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

6.  Stille cross-coupling reaction of an alpha-stannyl enamide.

Authors:  S Minière; J C Cintrat
Journal:  J Org Chem       Date:  2001-11-02       Impact factor: 4.354

7.  Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene-ynamide.

Authors:  Nozomi Saito; Yukako Sato; Miwako Mori
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

8.  Synthesis and reactivity of an alpha-stannyl beta-silyl enamide.

Authors:  Laurianne Timbart; Jean-Christophe Cintrat
Journal:  Chemistry       Date:  2002-04-02       Impact factor: 5.236

9.  A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.

Authors:  Michael O Frederick; Jason A Mulder; Michael R Tracey; Richard P Hsung; Jian Huang; Kimberly C M Kurtz; Lichun Shen; Christopher J Douglas
Journal:  J Am Chem Soc       Date:  2003-03-05       Impact factor: 15.419

10.  Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols.

Authors:  Michael O Frederick; Richard P Hsung; Robert H Lambeth; Jason A Mulder; Michael R Tracey
Journal:  Org Lett       Date:  2003-07-24       Impact factor: 6.005
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  20 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors:  Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

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.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

5.  Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors:  Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-10-28       Impact factor: 4.354

6.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

7.  Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.

Authors:  Joshua R Dunetz; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

8.  Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

Authors:  Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-09-03       Impact factor: 4.354

9.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007

10.  Synthesis of alpha-keto-imides via oxidation of ynamides.

Authors:  Ziyad F Al-Rashid; Whitney L Johnson; Richard P Hsung; Yonggang Wei; Pei-Yuan Yao; Renhei Liu; Kang Zhao
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354
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