Literature DB >> 20384303

N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes.

Akkattu T Biju1, Nathalie E Wurz, Frank Glorius.   

Abstract

The N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated alkynes to provide alpha,beta-unsaturated ketones is reported. In addition, a rare case of an efficient and selective dually NHC-catalyzed cascade reaction involving the hydroacylation of alkynes and a subsequent intermolecular Stetter reaction allows the formation of chromanones containing a 1,4-diketone moiety.

Entities:  

Year:  2010        PMID: 20384303     DOI: 10.1021/ja102130s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

Authors:  Peng Zhou; Wen-Juan Hao; Jin-Peng Zhang; Bo Jiang; Guigen Li; Shu-Jiang Tu
Journal:  Chem Commun (Camb)       Date:  2015-08-21       Impact factor: 6.222

3.  Organocatalytic hydroacylation of unactivated alkenes.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-30       Impact factor: 15.336

4.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

5.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

6.  Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis.

Authors:  Austin H Asari; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

7.  Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

Authors:  Qing-An Chen; Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2015-01-21       Impact factor: 15.419

8.  Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

Authors:  Satavisha Sarkar; Arghya Banerjee; Wang Yao; Eric V Patterson; Ming-Yu Ngai
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.084

9.  Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Authors:  Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-11       Impact factor: 16.383

10.  Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors:  Qing-An Chen; Daniel K Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

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